(2S,3R)-3-((4S,5S)-5-Benzyloxymethyl-2,2-dimethyl-[1,3]dioxolan-4-yl)-2-(tert-butyl-dimethyl-silanyloxymethyl)-2,3-dihydroxy-propionic acid methyl ester

Base Information

• Chemical Name: (2S,3R)-3-((4S,5S)-5-Benzyloxymethyl-2,2-dimethyl-[1,3]dioxolan-4-yl)-2-(tert-butyl-dimethyl-silanyloxymethyl)-2,3-dihydroxy-propionic acid methyl ester
• CAS No.: 357625-78-6
• Molecular Formula: C₂₄H₄₀O₈Si
• Molecular Weight: 484.662
• Mol file: 357625-78-6.mol

Synonyms:

Chemical Property of (2S,3R)-3-((4S,5S)-5-Benzyloxymethyl-2,2-dimethyl-[1,3]dioxolan-4-yl)-2-(tert-butyl-dimethyl-silanyloxymethyl)-2,3-dihydroxy-propionic acid methyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,3R)-3-((4S,5S)-5-Benzyloxymethyl-2,2-dimethyl-[1,3]dioxolan-4-yl)-2-(tert-butyl-dimethyl-silanyloxymethyl)-2,3-dihydroxy-propionic acid methyl ester

There total 4 articles about (2S,3R)-3-((4S,5S)-5-Benzyloxymethyl-2,2-dimethyl-[1,3]dioxolan-4-yl)-2-(tert-butyl-dimethyl-silanyloxymethyl)-2,3-dihydroxy-propionic acid methyl 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:

tert-butyldimethylsilyl chloride (18162-48-6) + (2S,3R)-3-((4S,5S)-5-Benzyloxymethyl-2,2-dimethyl-[1,3]dioxolan-4-yl)-2,3-dihydroxy-2-hydroxymethyl-propionic acid methyl ester (1053628-43-5) → (2S,3R)-3-((4S,5S)-5-Benzyloxymethyl-2,2-dimethyl-[1,3]dioxolan-4-yl)-2-(tert-butyl-dimethyl-silanyloxymethyl)-2,3-dihydroxy-propionic acid methyl ester (357625-78-6)

Guidance literature:

With dmap; triethylamine;

Reference yield:

C24H38O6Si (1197205-94-9) → C24H40O8Si (1197205-95-0) + (2S,3R)-3-((4S,5S)-5-Benzyloxymethyl-2,2-dimethyl-[1,3]dioxolan-4-yl)-2-(tert-butyl-dimethyl-silanyloxymethyl)-2,3-dihydroxy-propionic acid methyl ester (357625-78-6)

Guidance literature:

With methanesulfonamide; AD-mix β; In water; tert-butyl alcohol; at 20 ℃; for 48h; optical yield given as %de; stereoselective reaction; Inert atmosphere;

DOI:10.1002/ejoc.200900772

Reference yield:

(4S,5R)-4-benzyloxymethyl-2,2-dimethyl-1,3-dioxolane-5-carboxaldehyde (81028-12-8) → (2S,3R)-3-((4S,5S)-5-Benzyloxymethyl-2,2-dimethyl-[1,3]dioxolan-4-yl)-2-(tert-butyl-dimethyl-silanyloxymethyl)-2,3-dihydroxy-propionic acid methyl ester (357625-78-6)

Guidance literature:

Multi-step reaction with 3 steps

1: DABCO / 20 °C

2: aq. OsO₄; NMO / acetone / 20 °C

3: Et₃N; DMAP

With 1,4-diaza-bicyclo[2.2.2]octane; dmap; osmium(VIII) oxide; N-methyl-2-indolinone; triethylamine; In acetone; 1: Baylis-Hillman reaction;

upstream raw materials:

tert-butyldimethylsilyl chloride

(2S,3R)-3-((4S,5S)-5-Benzyloxymethyl-2,2-dimethyl-[1,3]dioxolan-4-yl)-2,3-dihydroxy-2-hydroxymethyl-propionic acid methyl ester

(4S,5R)-4-benzyloxymethyl-2,2-dimethyl-1,3-dioxolane-5-carboxaldehyde

2-[(S)-((4S,5S)-5-Benzyloxymethyl-2,2-dimethyl-[1,3]dioxolan-4-yl)-hydroxy-methyl]-acrylic acid methyl ester

Downstream raw materials:

(2S,3S)-3-((4R,5S)-5-Benzyloxymethyl-2,2-dimethyl-[1,3]dioxolan-4-yl)-2-(tert-butyl-dimethyl-silanyloxymethyl)-oxirane-2-carboxylic acid methyl ester

[(2S,3S)-3-((4R,5S)-5-Benzyloxymethyl-2,2-dimethyl-[1,3]dioxolan-4-yl)-2-(tert-butyl-dimethyl-silanyloxymethyl)-oxiranyl]-methanol

C₂₅H₄₂O₁₀SSi