1,3-Butanediol, 2-methyl-4-(phenylmethoxy)-, (2S,3R)-

Base Information

• Chemical Name: 1,3-Butanediol, 2-methyl-4-(phenylmethoxy)-, (2S,3R)-
• CAS No.: 86990-92-3
• Molecular Formula: C12H18O3
• Molecular Weight: 210.273
• DSSTox Substance ID: DTXSID70518723
• Nikkaji Number: J851.325B
• Mol file: 86990-92-3.mol

Synonyms:(2S,3R)-4-(Benzyloxy)-2-methylbutane-1,3-diol;86990-92-3;DTXSID70518723

Chemical Property of 1,3-Butanediol, 2-methyl-4-(phenylmethoxy)-, (2S,3R)-

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:

SDS file from LookChem

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 1,3-Butanediol, 2-methyl-4-(phenylmethoxy)-, (2S,3R)-

There total 17 articles about 1,3-Butanediol, 2-methyl-4-(phenylmethoxy)-, (2S,3R)- 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: 91.0%

trimethylaluminum (75-24-1) + ((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,3R)-4-(benzyloxy)-2-methylbutane-1,3-diol (86990-92-3)

Guidance literature:

((2R,3S)-3-((benzyloxy)methyl)oxiran-2-yl)methanol; With n-butyllithium; In hexane; dichloromethane; at 0 ℃; for 0.333333h; Inert atmosphere;

trimethylaluminum; In hexane; dichloromethane; toluene; at 0 ℃; for 0.166667h; regioselective reaction; Inert atmosphere;

DOI:10.1016/j.tetlet.2017.05.034

upstream raw materials:

lithium dimethylcuprate

cis-4-benzyloxy-2,3-epoxy-1-butanol

methylcopper

trimethylaluminum

Downstream raw materials:

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

bis[(9H-fluoren-9-yl)methyl](2S,3S,6S)-1-(4-methoxybenzyloxy)-2-methyl-6-((2S,3S)-3-methyl-6-oxo-3,6-dihydro-2H-pyran-2-yl)heptan-3-yl phosphate

(3R,4S,5S,6R)-6,7-(isopropylidenedioxy)-4-(4-methoxybenzyloxy)-3,5-dimethyl-1-heptene

(2S,3R,4S)-4-((R)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-3-(4-methoxy-benzyloxy)-2-methyl-pentanal