*,R^*)>-1-<<(tert-Butyldiphenylsilyl)oxy>methyl>-3,3-dimethyl-α-(2-furanyl)-2,4-dioxolane-5-methanol

Base Information

• Chemical Name: *,R^*)>-1-<<(tert-Butyldiphenylsilyl)oxy>methyl>-3,3-dimethyl-α-(2-furanyl)-2,4-dioxolane-5-methanol
• CAS No.: 147730-61-8
• Molecular Formula: C₂₇H₃₄O₅Si
• Molecular Weight: 466.649

Synonyms:

Chemical Property of *,R^*)>-1-<<(tert-Butyldiphenylsilyl)oxy>methyl>-3,3-dimethyl-α-(2-furanyl)-2,4-dioxolane-5-methanol

Chemical Property:

Purity/Quality:

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MSDS Files:

Useful:

Technology Process of *,R^*)>-1-<<(tert-Butyldiphenylsilyl)oxy>methyl>-3,3-dimethyl-α-(2-furanyl)-2,4-dioxolane-5-methanol

There total 4 articles about *,R^*)>-1-<<(tert-Butyldiphenylsilyl)oxy>methyl>-3,3-dimethyl-α-(2-furanyl)-2,4-dioxolane-5-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:

2,3-O-isopropylidene-L-threitol (50622-09-8) → *,R*)>-1-<<(tert-Butyldiphenylsilyl)oxy>methyl>-3,3-dimethyl-α-(2-furanyl)-2,4-dioxolane-5-methanol (147730-61-8)

Guidance literature:

Multi-step reaction with 3 steps

1: 1.) n-BuLi / 1.) THF, 0 deg C, 40 min, 2.) 0 deg C, 1 h, then r.t., 4 h

2: 1.) DMSO, oxalyl chloride, 2.) Et₃N / 1.) CH₂Cl₂, -78 deg C, 15 min, 2.) r.t., 1 h

3: 1.) n-BuLi, 2.) ZnBr₂ / 1.) THF, -10 deg C, 2 h, 2.) -20 to -25 deg C, 4 h

With n-butyllithium; oxalyl dichloride; dimethyl sulfoxide; triethylamine; zinc dibromide;

DOI:10.1021/jo00062a035

Reference yield:

4-O-(tert-butyldiphenylsilyl)-2,3-O-isopropylidene-L-threitol (136032-73-0,127251-09-6) → *,R*)>-1-<<(tert-Butyldiphenylsilyl)oxy>methyl>-3,3-dimethyl-α-(2-furanyl)-2,4-dioxolane-5-methanol (147730-61-8)

Guidance literature:

Multi-step reaction with 2 steps

1: 1.) DMSO, oxalyl chloride, 2.) Et₃N / 1.) CH₂Cl₂, -78 deg C, 15 min, 2.) r.t., 1 h

2: 1.) n-BuLi, 2.) ZnBr₂ / 1.) THF, -10 deg C, 2 h, 2.) -20 to -25 deg C, 4 h

With n-butyllithium; oxalyl dichloride; dimethyl sulfoxide; triethylamine; zinc dibromide;

DOI:10.1021/jo00062a035

Reference yield:

tert-butylchlorodiphenylsilane (58479-61-1) → *,R*)>-1-<<(tert-Butyldiphenylsilyl)oxy>methyl>-3,3-dimethyl-α-(2-furanyl)-2,4-dioxolane-5-methanol (147730-61-8)

Guidance literature:

Multi-step reaction with 3 steps

1: 1.) n-BuLi / 1.) THF, 0 deg C, 40 min, 2.) 0 deg C, 1 h, then r.t., 4 h

2: 1.) DMSO, oxalyl chloride, 2.) Et₃N / 1.) CH₂Cl₂, -78 deg C, 15 min, 2.) r.t., 1 h

3: 1.) n-BuLi, 2.) ZnBr₂ / 1.) THF, -10 deg C, 2 h, 2.) -20 to -25 deg C, 4 h

With n-butyllithium; oxalyl dichloride; dimethyl sulfoxide; triethylamine; zinc dibromide;

DOI:10.1021/jo00062a035

upstream raw materials:

furan

4-O-(tert-butyldiphenylsilyl)-2,3-O-isopropylidene-L-threose

2,3-O-isopropylidene-L-threitol

4-O-(tert-butyldiphenylsilyl)-2,3-O-isopropylidene-L-threitol

Downstream raw materials:

(2S,3R,6S)-2-[(4R,5S)-5-(tert-Butyl-diphenyl-silanyloxymethyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-6-methoxy-tetrahydro-pyran-3-ol

[(4S,5S)-5-((2S,3S,6S)-3-Azido-6-methoxy-tetrahydro-pyran-2-yl)-2,2-dimethyl-[1,3]dioxolan-4-ylmethoxy]-tert-butyl-diphenyl-silane

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