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

Base Information

• Chemical Name: [(2S,3S)-3-((4R,5S)-5-Benzyloxymethyl-2,2-dimethyl-[1,3]dioxolan-4-yl)-2-(tert-butyl-dimethyl-silanyloxymethyl)-oxiranyl]-methanol
• CAS No.: 357625-82-2
• Molecular Formula: C₂₃H₃₈O₆Si
• Molecular Weight: 438.637
• Mol file: 357625-82-2.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 8 articles about [(2S,3S)-3-((4R,5S)-5-Benzyloxymethyl-2,2-dimethyl-[1,3]dioxolan-4-yl)-2-(tert-butyl-dimethyl-silanyloxymethyl)-oxiranyl]-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:

(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 (357625-76-4) → [(2S,3S)-3-((4R,5S)-5-Benzyloxymethyl-2,2-dimethyl-[1,3]dioxolan-4-yl)-2-(tert-butyl-dimethyl-silanyloxymethyl)-oxiranyl]-methanol (357625-82-2)

Guidance literature:

With diisobutylaluminium hydride; In dichloromethane; at -78 ℃;

Reference yield:

C23H36O6Si → [(2S,3S)-3-((4R,5S)-5-Benzyloxymethyl-2,2-dimethyl-[1,3]dioxolan-4-yl)-2-(tert-butyl-dimethyl-silanyloxymethyl)-oxiranyl]-methanol (357625-82-2)

Guidance literature:

With sodium tetrahydroborate; In methanol; at 20 ℃; for 0.5h; 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,3S)-3-((4R,5S)-5-Benzyloxymethyl-2,2-dimethyl-[1,3]dioxolan-4-yl)-2-(tert-butyl-dimethyl-silanyloxymethyl)-oxiranyl]-methanol (357625-82-2)

Guidance literature:

Multi-step reaction with 6 steps

1: DABCO / 20 °C

2: aq. OsO₄; NMO / acetone / 20 °C

3: Et₃N; DMAP

4: pyridine / CH₂Cl₂ / 0 - 20 °C

5: K₂CO₃ / methanol / 20 °C

6: DIBAL-H / CH₂Cl₂ / -78 °C

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

upstream 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

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

tert-butyldimethylsilyl chloride

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

Downstream raw materials:

C₂₃H₃₇IO₅Si