(+)-1,4-Di-O-benzyl-D-threitol

Basic Information

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CAS Number

91604-41-0

Molecular Formula

C18H22O4

Molecular Weight

302.4 g/mol

Chemical Classification

Basic Chemical Raw Materials Organic Chemicals Ethers

Basic Physical Properties

Melting Point

56.0 to 59.0 deg-C

Boiling Point

484.4°C at 760 mmHg

Density

1.174±0.06 g/cm3 (20 ºC 760 Torr),

Flash Point

246.7°C

Refractive Index

6.3 ° (C=5, CHCl3)

SMILES

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C1=CC=C(C=C1)COCC(C(COCC2=CC=CC=C2)O)O

InChI

InChI=1S/C18H22O4/c19-17(13-21-11-15-7-3-1-4-8-15)18(20)14-22-12-16-9-5-2-6-10-16/h1-10,17-20H,11-14H2/t17-,18-/m1/s1

InChIKey

YAVAVQDYJARRAU-QZTJIDSGSA-N

LogP

2.141800000000001

Topological Polar Surface Area

58.92 Å²

Hydrogen Bond Donor/Acceptor

2 / 4

Complexity

244

Synonyms & References

English

MFCD00077722
D2239
1,4-di-O-benzylthreitol
(2R,3R)-1,4-bis(phenylmethoxy)butane-2,3-diol
(2R,3R)-(+)-1,4-Dibenzyloxy-2,3-butanediol, 98%
YAVAVQDYJARRAU-QZTJIDSGSA-N
AKOS015839323
(2R,3R)-1,4-bis(benzyloxy)butane-2,3-diol
AKOS015889570
T71452
91604-41-0
DTXSID10426474
2,3-Butanediol,1,4-bis(phenylmethoxy)-,(2R,3R)-
AS-64982
(R*,R*)-(+/-)-1,4-bis(phenylmethoxy)-2,3-butanediol
SCHEMBL93708
(+)-1,4-Di-O-benzyl-D-threitol
(+)-(2R,3R)-1,4-Bis(benzyloxy)-2,3-butanediol
2,3-Butanediol,1,4-bis(phenylmethoxy)-, (2R,3R)-
(2R,3R)-1,4-bis(Phenylmethoxy)-2,3-butanediol
(R,R)-1,4-Di-O-benzyl-D-threitol
1,4-Di-O-benzyl-D-threitol
(+)-1,4-Di-O-benzyl-D-threito
(2R,3R)-(+)-1,4-Dibenzyloxy-2,3-butanediol
PubChem8153
FCH3599923
CM10272
AS06324
AB1011213

MDL Number

MFCD00077722

FAQ

What are the physical and chemical properties of (+)-1,4-Di-O-benzyl-D-threitol (CAS: 91604-41-0)?

The (R)-enantiomer of (+)-1,4-Di-O-benzyl-D-threitol (CAS: 91604-41-0) is a white crystalline solid with a molecular weight of approximately 322.34 g/mol. It is poorly soluble in water but soluble in common organic solvents like chloroform and ethanol. This compound has a moderate reactivity towards nucleophiles and electrophiles. It can be used in organic synthesis as a chiral building block.

How is (+)-1,4-Di-O-benzyl-D-threitol (CAS: 91604-41-0) typically synthesized?

The (R)-enantiomer of (+)-1,4-Di-O-benzyl-D-threitol (CAS: 91604-41-0) can be synthesized via a stereoselective reaction of D-threitol with benzyl chloride in the presence of a Lewis acid catalyst. The reaction yields a high enantiomeric excess, typically greater than 99%, with good yield. This method is commonly used in the preparation of optically active compounds for pharmaceutical and biochemical applications.

What industries use (+)-1,4-Di-O-benzyl-D-threitol (CAS: 91604-41-0)?

The (R)-enantiomer of (+)-1,4-Di-O-benzyl-D-threitol (CAS: 91604-41-0) is widely used in the pharmaceutical industry for the synthesis of chiral drugs. It is also utilized in the polymer industry for the development of advanced materials and in the sensor industry for the construction of biosensors. Additionally, it has applications in the semiconductor industry as a chiral ligand in metal-organic chemical vapor deposition (MOCVD) processes.

What precautions should be taken when handling (+)-1,4-Di-O-benzyl-D-threitol (CAS: 91604-41-0)?

When handling (+)-1,4-Di-O-benzyl-D-threitol (CAS: 91604-41-0), it is essential to use appropriate personal protective equipment (PPE), such as gloves, safety goggles, and a lab coat. Work should be performed in a well-ventilated hood to minimize inhalation risks. In case of a spill, immediately clean up with appropriate absorbent materials and dispose of in a hazardous waste container. Always refer to the safety data sheet (SDS) for detailed handling and emergency procedures.