(3S,4S,5S)-6-(tert-Butyl-diphenyl-silanyloxy)-3,4-dihydroxy-5-iodo-hexanoic acid methyl ester

Base Information

• Chemical Name: (3S,4S,5S)-6-(tert-Butyl-diphenyl-silanyloxy)-3,4-dihydroxy-5-iodo-hexanoic acid methyl ester
• CAS No.: 204328-41-6
• Molecular Formula: C₂₃H₃₁IO₅Si
• Molecular Weight: 542.486
• Mol file: 204328-41-6.mol

Synonyms:(3S,4S,5S)-6-(tert-Butyl-diphenyl-silanyloxy)-3,4-dihydroxy-5-iodo-hexanoic acid methyl ester

Chemical Property of (3S,4S,5S)-6-(tert-Butyl-diphenyl-silanyloxy)-3,4-dihydroxy-5-iodo-hexanoic acid methyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3S,4S,5S)-6-(tert-Butyl-diphenyl-silanyloxy)-3,4-dihydroxy-5-iodo-hexanoic acid methyl ester

There total 2 articles about (3S,4S,5S)-6-(tert-Butyl-diphenyl-silanyloxy)-3,4-dihydroxy-5-iodo-hexanoic 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: 80.0%

(S)-3-[(2R,3S)-3-(tert-Butyl-diphenyl-silanyloxymethyl)-oxiranyl]-3-hydroxy-propionic acid methyl ester → (3S,4S,5S)-6-(tert-Butyl-diphenyl-silanyloxy)-3,4-dihydroxy-5-iodo-hexanoic acid methyl ester (204328-41-6)

Guidance literature:

With magnesium iodide; In toluene; at -78 ℃; for 19h;

DOI:10.1021/jo972116s

Reference yield:

(2R,3R)-4-(tert-Butyldiphenylsilyloxy)-2,3-epoxybutan-1-al (131380-35-3) → (3S,4S,5S)-6-(tert-Butyl-diphenyl-silanyloxy)-3,4-dihydroxy-5-iodo-hexanoic acid methyl ester (204328-41-6)

Guidance literature:

Multi-step reaction with 2 steps

1: 79 percent

2: 80 percent / magnesium iodide / toluene / 19 h / -78 °C

With magnesium iodide; In toluene;

DOI:10.1021/jo972116s

Reference yield: 98.0%

chloro-trimethyl-silane (75-77-4) + (3S,4S,5S)-6-(tert-Butyl-diphenyl-silanyloxy)-3,4-dihydroxy-5-iodo-hexanoic acid methyl ester (204328-41-6) → (3S,4S,5S)-6-(tert-Butyl-diphenyl-silanyloxy)-5-iodo-3,4-bis-trimethylsilanyloxy-hexanoic acid methyl ester (204328-43-8)

Guidance literature:

With pyridine; 1,1,1,3,3,3-hexamethyl-disilazane; for 12h;

DOI:10.1021/jo972116s

upstream raw materials:

(2R,3R)-4-(tert-Butyldiphenylsilyloxy)-2,3-epoxybutan-1-al

Downstream raw materials:

(3S,4S,5S)-6-(tert-Butyl-diphenyl-silanyloxy)-5-iodo-3,4-bis-trimethylsilanyloxy-hexanoic acid methyl ester

(4S,5R)-5-[(R)-1-Azido-2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-4-hydroxy-dihydro-furan-2-one