(2R,3S)-2-Methyl-4-(phenylmethoxy)-1,3-butanediol

Base Information

• Chemical Name: (2R,3S)-2-Methyl-4-(phenylmethoxy)-1,3-butanediol
• CAS No.: 107441-62-3
• Molecular Formula: C₁₂H₁₈O₃
• Molecular Weight: 210.273
• DSSTox Substance ID: DTXSID101233150
• Nikkaji Number: J1.478.287G
• Mol file: 107441-62-3.mol

Synonyms:DTXSID101233150;107441-62-3;(2R,3S)-2-Methyl-4-(phenylmethoxy)-1,3-butanediol

Chemical Property of (2R,3S)-2-Methyl-4-(phenylmethoxy)-1,3-butanediol

Chemical Property:

• XLogP3: 1.1
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 6
• Exact Mass: 210.125594432
• Heavy Atom Count: 15
• Complexity: 155

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CC(CO)C(COCC1=CC=CC=C1)O
• Isomeric SMILES: C[C@H](CO)[C@@H](COCC1=CC=CC=C1)O

Technology Process of (2R,3S)-2-Methyl-4-(phenylmethoxy)-1,3-butanediol

There total 13 articles about (2R,3S)-2-Methyl-4-(phenylmethoxy)-1,3-butanediol 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: 96.0%

trimethylaluminum (75-24-1) + cis-4-benzyloxy-2,3-epoxy-1-butanol (87172-27-8) → (2S,3R)-4-Benzyloxy-2-methyl-butane-1,3-diol (86990-89-8,86990-92-3,107441-62-3,117112-54-6,130321-90-3)

Guidance literature:

cis-4-benzyloxy-2,3-epoxy-1-butanol; With n-butyllithium; In dichloromethane;

trimethylaluminum; In dichloromethane; at 0 - 20 ℃; Further stages.;

DOI:10.1021/ol010062+

Reference yield: 94.0%

methylcopper (1184-53-8) + cis-4-benzyloxy-2,3-epoxy-1-butanol (87172-27-8) → (2S,3R)-4-Benzyloxy-2-methyl-butane-1,3-diol (86990-89-8,86990-92-3,107441-62-3,117112-54-6,130321-90-3) + (2R,3S)-4-Benzyloxy-3-methyl-butane-1,2-diol (59005-41-3,78479-16-0,80184-02-7,81422-90-4,117112-55-7,130321-91-4) + 1-benzyloxy-2,3-dihydroxypentane (99666-03-2,99745-03-6,117248-14-3,130404-14-7)

Guidance literature:

With n-butyllithium; lithium chloride; In tetrahydrofuran; various nucleophiles, other time;

Reference yield: 81.0%

(2S,3S)-1-((S)-4-benzyl-2-thioxothiazolidin-3-yl)-4-(benzyloxy)-3-hydroxy-2-methylbutan-1-one → (2R,3S)-4-(benzyloxy)-2-methylbutane-1,3-diol (107441-62-3)

Guidance literature:

With sodium tetrahydroborate; In tetrahydrofuran; ethanol; at 20 ℃; for 3h;

DOI:10.1002/anie.201209863

upstream raw materials:

(4S,5R)-4-Benzyloxymethyl-2,2,5-trimethyl-[1,3]dioxane

trimethylaluminum

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

lithium dimethylcuprate

Downstream raw materials:

2-{(2E,4E)-(1S,6S,7S)-1-[(S)-2-(tert-Butyl-diphenyl-silanyloxy)-1-methyl-ethyl]-7-methoxy-4,6-dimethyl-8-phenyl-octa-2,4-dienyl}-isoindole-1,3-dione

2-{(2E,4E)-(1S,6S,7S)-1-[(S)-2-(tert-Butyl-diphenyl-silanyloxy)-1-methyl-ethyl]-7-methoxy-4,6-dimethyl-8-phenyl-octa-2,4-dienyl}-isoindole-1,3-dione

2-[(1R,2S)-1-Benzyloxymethyl-3-(tert-butyl-diphenyl-silanyloxy)-2-methyl-propyl]-isoindole-1,3-dione

(4E,6E)-(2S,3S,8S,9S)-3-(1,3-Dioxo-1,3-dihydro-isoindol-2-yl)-9-methoxy-2,6,8-trimethyl-10-phenyl-deca-4,6-dienoic acid methyl ester