Methanesulfonic acid (4S,5S)-5-(tert-butyl-diphenyl-silanyloxymethyl)-2,2-dimethyl-[1,3]dioxolan-4-ylmethyl ester

Base Information

• Chemical Name: Methanesulfonic acid (4S,5S)-5-(tert-butyl-diphenyl-silanyloxymethyl)-2,2-dimethyl-[1,3]dioxolan-4-ylmethyl ester
• CAS No.: 127251-04-1
• Molecular Formula: C₂₄H₃₄O₆SSi
• Molecular Weight: 478.682

Synonyms:Methanesulfonic acid (4S,5S)-5-(tert-butyl-diphenyl-silanyloxymethyl)-2,2-dimethyl-[1,3]dioxolan-4-ylmethyl ester

Chemical Property of Methanesulfonic acid (4S,5S)-5-(tert-butyl-diphenyl-silanyloxymethyl)-2,2-dimethyl-[1,3]dioxolan-4-ylmethyl ester

Chemical Property:

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Technology Process of Methanesulfonic acid (4S,5S)-5-(tert-butyl-diphenyl-silanyloxymethyl)-2,2-dimethyl-[1,3]dioxolan-4-ylmethyl ester

There total 3 articles about Methanesulfonic acid (4S,5S)-5-(tert-butyl-diphenyl-silanyloxymethyl)-2,2-dimethyl-[1,3]dioxolan-4-ylmethyl ester 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: 90.0%

4-O-(tert-butyldiphenylsilyl)-2,3-O-isopropylidene-L-threitol (136032-73-0,127251-09-6) + methanesulfonyl chloride (124-63-0) → Methanesulfonic acid (4S,5S)-5-(tert-butyl-diphenyl-silanyloxymethyl)-2,2-dimethyl-[1,3]dioxolan-4-ylmethyl ester (127251-04-1)

Guidance literature:

With triethylamine; In dichloromethane; at -10 ℃; for 0.75h;

DOI:10.1016/S0040-4039(01)80698-5

Reference yield:

2,3-O-isopropylidene-L-threitol (50622-09-8) → Methanesulfonic acid (4S,5S)-5-(tert-butyl-diphenyl-silanyloxymethyl)-2,2-dimethyl-[1,3]dioxolan-4-ylmethyl ester (127251-04-1)

Guidance literature:

Multi-step reaction with 2 steps

1: NaH / tetrahydrofuran / 20 °C

2: 90 percent / Et₃N / CH₂Cl₂ / 0.75 h / -10 °C

With sodium hydride; triethylamine; In tetrahydrofuran; dichloromethane;

DOI:10.1016/S0040-4039(01)80698-5

Reference yield:

tert-butylchlorodiphenylsilane (58479-61-1) → Methanesulfonic acid (4S,5S)-5-(tert-butyl-diphenyl-silanyloxymethyl)-2,2-dimethyl-[1,3]dioxolan-4-ylmethyl ester (127251-04-1)

Guidance literature:

Multi-step reaction with 2 steps

1: NaH / tetrahydrofuran / 20 °C

2: 90 percent / Et₃N / CH₂Cl₂ / 0.75 h / -10 °C

With sodium hydride; triethylamine; In tetrahydrofuran; dichloromethane;

DOI:10.1016/S0040-4039(01)80698-5

upstream raw materials:

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

methanesulfonyl chloride

2,3-O-isopropylidene-L-threitol

tert-butylchlorodiphenylsilane

Downstream raw materials:

tert-Butyl-((4S,5R)-5-iodomethyl-2,2-dimethyl-[1,3]dioxolan-4-ylmethoxy)-diphenyl-silane

[(4S,5S)-5-(tert-Butyl-diphenyl-silanyloxymethyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-acetaldehyde

[(4S,5S)-5-(tert-Butyl-diphenyl-silanyloxymethyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-acetonitrile

Benzoic acid (S)-1-{(E)-2-[(4S,5S)-2,2-dimethyl-5-((Z)-pent-2-enyl)-[1,3]dioxolan-4-yl]-vinyl}-8-methoxycarbonyl-octyl ester

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