(5S,5aR,8aR,9R)-9-(4-Hydroxy-3,5-dimethoxyphenyl)-8-oxo-5,5a,6,8,8a,9-hexahydrofuro[3',4':6,7]naphtho[2,3-d][1,3]dioxol-5-yl 4,6-O-(2-thienylmethylene)-beta-D-glucopyranoside

Basic Information

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CAS Number

29767-20-2

Molecular Formula

C32H32O13S

Molecular Weight

656.66 g/mol

Chemical Classification

Basic Chemical Raw Materials Organic Chemicals Carboxylic Acids

Basic Chemical Raw Materials Organic Chemicals Esters

Basic Chemical Raw Materials Organic Chemicals Ethers

Basic Chemical Raw Materials Organic Chemicals Heterocyclic Compounds

Pharmaceutical Chemicals Pharmaceutical Intermediates Heterocyclic Intermediates

Fine Chemicals Dyes and Pigments Organic Dyes

Fine Chemicals Surfactants Anionic Surfactants

Laboratory Chemicals Research Chemicals Biochemical Reagents

Basic Physical Properties

Melting Point

242-246°C

Boiling Point

864.3°C at 760 mmHg

Solubility

DMSO: soluble10mg/mL, clear

Refractive Index

1.5530 (estimate)

Specific Rotation

-107°(9:1 chloroform/methanol)

SMILES

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COC1=CC(=CC(=C1O)OC)C2C3C(COC3=O)C(C4=CC5=C(C=C24)OCO5)OC6C(C(C7C(O6)COC(O7)C8=CC=CS8)O)O

InChI

InChI=1S/C32H32O13S/c1-37-19-6-13(7-20(38-2)25(19)33)23-14-8-17-18(42-12-41-17)9-15(14)28(16-10-39-30(36)24(16)23)44-32-27(35)26(34)29-21(43-32)11-40-31(45-29)22-4-3-5-46-22/h3-9,16,21,23-24,26-29,31-35H,10-12H2,1-2H3/t16-,21+,23+,24-,26+,27+,28+,29+,31?,32-/m0/s1

InChIKey

NRUKOCRGYNPUPR-PSZSYXFXSA-N

LogP

2.7529000000000003

pKa

10.13(at 25℃)

Topological Polar Surface Area

160.83 Å²

Hydrogen Bond Donor/Acceptor

3 / 13

Complexity

1090

Safety Information

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Hazard Statement

H341 Suspected of causing genetic defects
Germ cell mutagenicity

H350 May cause cancer
Carcinogenicity

H361 Suspected of damaging fertility or the unborn child
Reproductive toxicity

H371 May cause damage to organs
Specific target organ toxicity, single exposure

H372 Causes damage to organs through prolonged or repeated exposure
Specific target organ toxicity, repeated exposure

Synonyms & References

English

Epipodophyllotoxin-beta-D-thenylidene-glucoside, 4'-demethyl-
4'-Demethylepipodophyllotoxin 9-(4,6-O-(R)-2-thenylidene-beta-D-glucopyranoside)
Teniposide- Bio-X
AB01274729-01
GTPL6843
Teniposido
NSC758255
TENIPOSIDE [IARC]
957E6438QA
s1787
NSC-122819
DTXSID8023638
VM-26
Q417555
(5S,5aR,8aR,9R)-5-[[(2R,4aR,6R,7R,8R,8aS)-7,8-dihydroxy-2-(2-thienyl)-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxin-6-yl]oxy]-9-(4-hydroxy-3,5-dimethoxy-phenyl)-5a,6,8a,9-tetrahydro-5H-isobenzofuro[6,5-f][1,3]benzodioxol-8-one
(10R,11R,15R,16S)-16-{[(2R,4aR,6R,7R,8R,8aS)-7,8-dihydroxy-2-(thiophen-2-yl)-hexahydro-2H-pyrano[3,2-d][1,3]dioxin-6-yl]oxy}-10-(4-hydroxy-3,5-dimethoxyphenyl)-4,6,13-trioxatetracyclo[7.7.0.0^{3,7}.0^{11,15}]hexadeca-1(9),2,7-trien-12-one
CHEMBL452231
4'-DEMETHYLEPIPODOPHYLLOTOXIN 9-(4,6-O-(R)-2-THENYLIDENE-.BETA.-D-GLUCOPYRANOSIDE)
Teniposidum
NSC 122819
HSDB 6546
4'-Dimethyl-9-(4,6-O-2-thenyid)-epipodophyllotoxin
MFCD00866516
FURO(3',4':6,7)NAPHTHO(2,3-D)-1,3-DIOXOL-6(5AH)-ONE, 5,8,8A,9-TETRAHYDRO-5-(4-HYDROXY-3,5-DIMETHOXYPHENYL)-9-((4,6-O-(2-THIENYLMETHYLENE)-.BETA.-D-GLUCOPYRANOSYL)-OXY)-, (5R-(5.ALPHA.,5A.BETA.,8A.ALPHA.,9.BETA.(R*)))
TENIPOSIDE [VANDF]
NSC-758255
Furo[3',4':6,7]naphtho[2,3-d]-1,3-dioxol-6(5aH)-one, 5,8,8a,9-tetrahydro-5-(4-hydroxy-3,5-dimethoxyphenyl)-9-[[4,6-O-[(R)-2-thienylmethylene]-.beta.-D-glucopyranosyl]oxy]-, (5R,5aR,8aR,9S)-
5-[[(6R)-7,8-dihydroxy-2-thiophen-2-yl-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxin-6-yl]oxy]-9-(4-hydroxy-3,5-dimethoxyphenyl)-5a,6,8a,9-tetrahydro-5H-[2]benzofuro[6,5-f][1,3]benzodioxol-8-one
TENIPOSIDE [MI]
Teniposide [USAN]
SCHEMBL3908

MDL Number

MFCD00866516

FAQ

What are the physical and chemical properties of (5S,5aR,8aR,9R)-9-(4-Hydroxy-3,5-dimethoxyphenyl)-8-oxo-5,5a,6,8,8a,9-hexahydrofuro[3',4':6,7]naphtho[2,3-d][1,3]dioxol-5-yl 4,6-O-(2-thienylmethylene)-beta-D-glucopyranoside (CAS: 29767-20-2)?

The compound is a sugar derivative with a complex molecular structure. Its molecular weight is approximately 606.31 g/mol, and it has a crystalline form. It is poorly soluble in water but soluble in methanol and ethanol. The compound is reactive towards nucleophiles and can undergo ring-opening reactions. It is stable under normal conditions but can degrade under acidic or strongly basic conditions.

How is (5S,5aR,8aR,9R)-9-(4-Hydroxy-3,5-dimethoxyphenyl)-8-oxo-5,5a,6,8,8a,9-hexahydrofuro[3',4':6,7]naphtho[2,3-d][1,3]dioxol-5-yl 4,6-O-(2-thienylmethylene)-beta-D-glucopyranoside (CAS: 29767-20-2) typically synthesized?

The compound is typically synthesized through a multistep process involving the protection of the hydroxyl groups, followed by ring-opening reactions, and finally, the glycosylation step. Commonly used catalysts include Lewis acids, and the overall yield is moderate. The synthetic route involves protecting reagents and careful control of reaction conditions to ensure high selectivity.

What industries use (5S,5aR,8aR,9R)-9-(4-Hydroxy-3,5-dimethoxyphenyl)-8-oxo-5,5a,6,8,8a,9-hexahydrofuro[3',4':6,7]naphtho[2,3-d][1,3]dioxol-5-yl 4,6-O-(2-thienylmethylene)-beta-D-glucopyranoside (CAS: 29767-20-2)?

This compound is primarily used in the pharmaceutical industry for drug development due to its specific chemical structure. It can also find applications in the polymer industry for the production of advanced materials, in sensor technology for detecting specific chemical compounds, and in semiconductor manufacturing for certain process steps. Its unique properties make it valuable in these sectors.

What precautions should be taken when handling (5S,5aR,8aR,9R)-9-(4-Hydroxy-3,5-dimethoxyphenyl)-8-oxo-5,5a,6,8,8a,9-hexahydrofuro[3',4':6,7]naphtho[2,3-d][1,3]dioxol-5-yl 4,6-O-(2-thienylmethylene)-beta-D-glucopyranoside (CAS: 29767-20-2)?

When handling this compound, safety goggles and gloves should be worn, and it should be conducted in a fume hood. Avoid contact with skin and eyes. In case of a spill, neutralize with a suitable reagent and dispose of according to local regulations. Always consult the Safety Data Sheet (SDS) for detailed handling instructions and emergency procedures.