(2s,3s)-4-(Phenylmethoxy)-1,2,3-butanetriol

Base Information

• Chemical Name: (2s,3s)-4-(Phenylmethoxy)-1,2,3-butanetriol
• CAS No.: 81028-07-1
• Molecular Formula: C₁₁H₁₆O₄
• Molecular Weight: 212.246
• DSSTox Substance ID: DTXSID101263246
• Mol file: 81028-07-1.mol

Synonyms:81028-07-1;(2s,3s)-4-(phenylmethoxy)-1,2,3-butanetriol;SCHEMBL13595511;DTXSID101263246

Chemical Property of (2s,3s)-4-(Phenylmethoxy)-1,2,3-butanetriol

Chemical Property:

• XLogP3: -0.3
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 6
• Exact Mass: 212.10485899
• Heavy Atom Count: 15
• Complexity: 157

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C(C=C1)COCC(C(CO)O)O
• Isomeric SMILES: C1=CC=C(C=C1)COC[C@@H]([C@H](CO)O)O

Technology Process of (2s,3s)-4-(Phenylmethoxy)-1,2,3-butanetriol

There total 9 articles about (2s,3s)-4-(Phenylmethoxy)-1,2,3-butanetriol which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 81.0%

(4S,5S)-4-benzyloxymethyl-5-hydroxymethyl-2,2-dimethyl-1,3-dioxolane (78469-77-9,81076-11-1,128820-40-6,78513-03-8) → (2S,3S)-1-(benzyloxy)butane-2,3,4-triol (81028-07-1)

Guidance literature:

With dowex 50Wx₈; In methanol; Ambient temperature;

DOI:10.1080/00397919408011189

Reference yield:

4-benzyloxy-2,3-O-isoproylidene-L-threitol (127896-23-5) → (2S,3S)-1-(benzyloxy)butane-2,3,4-triol (81028-07-1)

Guidance literature:

With copper dichloride; In acetonitrile; at 20 ℃; for 3h;

Reference yield:

((2R,3S)-3-((benzyloxy)methyl)oxiran-2-yl)methanol (78513-07-2,78513-12-9,78513-15-2,84621-89-6,87172-27-8,95672-91-6,98048-62-5,98048-63-6,78469-85-9) → (2S,3S)-1-(benzyloxy)butane-2,3,4-triol (81028-07-1)

Guidance literature:

With sodium hydroxide; In tert-butyl alcohol; Heating;

upstream raw materials:

(4S,5S)-4-benzyloxymethyl-5-hydroxymethyl-2,2-dimethyl-1,3-dioxolane

(2S,3R)-4-benzyloxy-2,3-(propane-2,2-dioxy)-1-butanol

(2S,3S)-4-benzyloxy-1,2,3-butanetriol

((2R,3S)-3-((benzyloxy)methyl)oxiran-2-yl)methanol

Downstream raw materials:

(2S,3S)-4-benzyloxy-1,2,3-butanetriol

threitol

4-benzyloxy-1,2,3-tri(tert-butyldimethylsilyloxy)-L-threitol