[(4'S,5'S)-5'-(benzyloxy)-2',2'-dimethyl-1',3'-dioxan-4'-yl]methanol

Base Information

• Chemical Name: [(4'S,5'S)-5'-(benzyloxy)-2',2'-dimethyl-1',3'-dioxan-4'-yl]methanol
• CAS No.: 100906-46-5
• Molecular Formula: C₁₄H₂₀O₄
• Molecular Weight: 252.31
• Mol file: 100906-46-5.mol

Synonyms:[(4'S,5'S)-5'-(benzyloxy)-2',2'-dimethyl-1',3'-dioxan-4'-yl]methanol

Chemical Property of [(4'S,5'S)-5'-(benzyloxy)-2',2'-dimethyl-1',3'-dioxan-4'-yl]methanol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of [(4'S,5'S)-5'-(benzyloxy)-2',2'-dimethyl-1',3'-dioxan-4'-yl]methanol

There total 11 articles about [(4'S,5'S)-5'-(benzyloxy)-2',2'-dimethyl-1',3'-dioxan-4'-yl]methanol 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: 95.0%

[(4'S,5'S)-5'-(benzyloxy)-2',2'-dimethyl-1',3'-dioxan-4'-yl]methyl benzoate → [(4'S,5'S)-5'-(benzyloxy)-2',2'-dimethyl-1',3'-dioxan-4'-yl]methanol (100906-46-5)

Guidance literature:

With ethanol; potassium carbonate; at 0 - 20 ℃; for 4.25h;

DOI:10.1016/j.carres.2014.11.004

Reference yield: 24.0%

2-Methoxypropene (116-11-0) + 2-O-benzyl-L-threitol (84379-51-1,84379-52-2,124909-02-0,127000-44-6) → 2-O-benzyl-3,4-O-isopropylidene-L-threitol (84379-53-3) + [(4'S,5'S)-5'-(benzyloxy)-2',2'-dimethyl-1',3'-dioxan-4'-yl]methanol (100906-46-5) + (5S,6S)-6-(benzyloxy)-2,2-dimethyl-1,3-dioxepan-5-ol (100906-45-4)

Guidance literature:

With pyridinium p-toluenesulfonate; In N,N-dimethyl-formamide; at -15 - 20 ℃; for 6h; Overall yield = 68 %; Overall yield = 16.54 g;

DOI:10.1016/j.carres.2014.11.004

Reference yield:

benzaldehyde (100-52-7) → [(4'S,5'S)-5'-(benzyloxy)-2',2'-dimethyl-1',3'-dioxan-4'-yl]methanol (100906-46-5)

Guidance literature:

Multi-step reaction with 3 steps

1: 91 percent / p-toluensulfonic acid / benzene / Heating

2: 93 percent / LiAlH₄, AlCl₃

3: p-toluensulfonic acid / dimethylformamide

With lithium aluminium tetrahydride; aluminium trichloride; toluene-4-sulfonic acid; In N,N-dimethyl-formamide; benzene;

DOI:10.1016/S0040-4039(00)89235-7

upstream raw materials:

2-Methoxypropene

2-O-benzyl-L-threitol

4,5-trans-bis(methoxycarbonyl)-2-phenyl-1,3-dioxolan

benzaldehyde

Downstream raw materials:

{[(4S,5S)-5-(benzyloxy)-2,2-dimethyl-1,3-dioxan-4-yl]methoxy}(tert-butyl)diphenylsilane