(2S,3R,4R,5S)-1-O-benzyl-3-O-(tert-butyldimethylsilyl)-2,4,6-trimethyl-6-heptene-1,3,5-triol

Base Information

• Chemical Name: (2S,3R,4R,5S)-1-O-benzyl-3-O-(tert-butyldimethylsilyl)-2,4,6-trimethyl-6-heptene-1,3,5-triol
• CAS No.: 131589-19-0
• Molecular Formula: C₂₃H₄₀O₃Si
• Molecular Weight: 392.654
• Mol file: 131589-19-0.mol

Synonyms:(2S,3R,4R,5S)-1-O-benzyl-3-O-(tert-butyldimethylsilyl)-2,4,6-trimethyl-6-heptene-1,3,5-triol

Chemical Property of (2S,3R,4R,5S)-1-O-benzyl-3-O-(tert-butyldimethylsilyl)-2,4,6-trimethyl-6-heptene-1,3,5-triol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,3R,4R,5S)-1-O-benzyl-3-O-(tert-butyldimethylsilyl)-2,4,6-trimethyl-6-heptene-1,3,5-triol

There total 5 articles about (2S,3R,4R,5S)-1-O-benzyl-3-O-(tert-butyldimethylsilyl)-2,4,6-trimethyl-6-heptene-1,3,5-triol 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: 12.0%

isopropenylmagnesium bromide (13291-18-4) + (2S,3R,4S)-5-Benzyloxy-3-(tert-butyl-dimethyl-silanyloxy)-2,4-dimethyl-pentanal (131722-56-0) → (2S,3R,4R,5R)-1-O-benzyl-3-O-(tert-butyldimethylsilyl)-2,4,6-trimethyl-6-heptene-1,3,5-triol (131681-61-3) + (2S,3R,4R,5S)-1-O-benzyl-3-O-(tert-butyldimethylsilyl)-2,4,6-trimethyl-6-heptene-1,3,5-triol (131589-19-0)

Guidance literature:

In diethyl ether; at 22 ℃; for 2h;

DOI:10.1021/ja00003a026

Reference yield:

benzyl bromide (100-39-0) → (2S,3R,4R,5S)-1-O-benzyl-3-O-(tert-butyldimethylsilyl)-2,4,6-trimethyl-6-heptene-1,3,5-triol (131589-19-0)

Guidance literature:

Multi-step reaction with 4 steps

1: 1.) NaH / 1.) DMF, 0 deg C, 2.) from -50 deg C to RT, overnight

2: 98 percent / imidazole / dimethylformamide / 48 h / 60 °C

3: 1.) ozone, 2.) Ph₃P / 1.) CH₂Cl₂, -78 deg C, 2.) from -78 deg C to RT

4: 61 percent / diethyl ether / 2 h / 22 °C

With 1H-imidazole; sodium hydride; ozone; triphenylphosphine; In diethyl ether; N,N-dimethyl-formamide;

DOI:10.1021/ja00003a026

Reference yield:

(2S,3S,4R)-1-benzyloxy-2,4-dimethylhex-5-ene-3-ol (106357-31-7) → (2S,3R,4R,5S)-1-O-benzyl-3-O-(tert-butyldimethylsilyl)-2,4,6-trimethyl-6-heptene-1,3,5-triol (131589-19-0)

Guidance literature:

Multi-step reaction with 3 steps

1: 98 percent / imidazole / dimethylformamide / 48 h / 60 °C

2: 1.) ozone, 2.) Ph₃P / 1.) CH₂Cl₂, -78 deg C, 2.) from -78 deg C to RT

3: 61 percent / diethyl ether / 2 h / 22 °C

With 1H-imidazole; ozone; triphenylphosphine; In diethyl ether; N,N-dimethyl-formamide;

DOI:10.1021/ja00003a026

upstream raw materials:

isopropenylmagnesium bromide

(2S,3R,4S)-5-Benzyloxy-3-(tert-butyl-dimethyl-silanyloxy)-2,4-dimethyl-pentanal

benzyl bromide

(2S,3S,4R)-1-benzyloxy-2,4-dimethylhex-5-ene-3-ol

Downstream raw materials:

(2S,3R,4S,5R,6R,7S,10S,11R,12R,13R)-1,11-di-O-benzyl-13-O-(tert-butyldimethylsilyl)-2,4,6,8,10,12-hexamethyl-3,5-O-isopropylidene-7-(thiophenoxy)-8(E)-pentadecene-1,3,5,6,11,13-hexol

(2S,3R,4S,5R,6R,7R,10S,11R,12R,13R)-1,11-di-O-benzyl-13-O-(tert-butyldimethylsilyl)-2,4,6,8,10,12-hexamethyl-3,5-O-isopropylidene-7-(thiophenoxy)-8(E)-pentadecene-1,3,5,6,11,13-hexol

(2S,3R,4S,5R,6S,7S,10S,11R,12R,13R)-1,11-di-O-benzyl-13-O-(tert-butyldimethylsilyl)-2,4,6,8,10,12-hexamethyl-3,5-O-isopropylidene-7-(thiophenoxy)-8(E)-pentadecene-1,3,5,6,11,13-hexol

(2S,3R,4S,5R,6S,7R,10S,11R,12R,13R)-1,11-di-O-benzyl-13-O-(tert-butyldimethylsilyl)-2,4,6,8,10,12-hexamethyl-3,5-O-isopropylidene-7-(thiophenoxy)-8(E)-pentadecene-1,3,5,6,11,13-hexol