(4S,5S,6S,9R)-6-Benzyloxy-9-(tert-butyl-diphenyl-silanyloxymethyl)-2,5-dimethyl-undec-1-en-4-ol

Base Information

• Chemical Name: (4S,5S,6S,9R)-6-Benzyloxy-9-(tert-butyl-diphenyl-silanyloxymethyl)-2,5-dimethyl-undec-1-en-4-ol
• CAS No.: 187862-60-8
• Molecular Formula: C₃₇H₅₂O₃Si
• Molecular Weight: 572.904
• Mol file: 187862-60-8.mol

Synonyms:(4S,5S,6S,9R)-6-Benzyloxy-9-(tert-butyl-diphenyl-silanyloxymethyl)-2,5-dimethyl-undec-1-en-4-ol

Chemical Property of (4S,5S,6S,9R)-6-Benzyloxy-9-(tert-butyl-diphenyl-silanyloxymethyl)-2,5-dimethyl-undec-1-en-4-ol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (4S,5S,6S,9R)-6-Benzyloxy-9-(tert-butyl-diphenyl-silanyloxymethyl)-2,5-dimethyl-undec-1-en-4-ol

There total 19 articles about (4S,5S,6S,9R)-6-Benzyloxy-9-(tert-butyl-diphenyl-silanyloxymethyl)-2,5-dimethyl-undec-1-en-4-ol 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: 71.0%

dimethyl-(2-methyl-2-propenyl)phenylsilane (34697-70-6) + (2R,3S,6R)-3-Benzyloxy-6-(tert-butyl-diphenyl-silanyloxymethyl)-2-methyl-octanal (187862-57-3) → (4S,5S,6S,9R)-6-Benzyloxy-9-(tert-butyl-diphenyl-silanyloxymethyl)-2,5-dimethyl-undec-1-en-4-ol (187862-60-8) + (4R,5S,6S,9R)-6-Benzyloxy-9-(tert-butyl-diphenyl-silanyloxymethyl)-2,5-dimethyl-undec-1-en-4-ol

Guidance literature:

With titanium tetrachloride; In dichloromethane; at -78 ℃; for 1h;

DOI:10.1021/jo001767c

Reference yield: 71.0%

dimethyl-(2-methyl-2-propenyl)phenylsilane (34697-70-6) + (2R,3S,6R)-3-Benzyloxy-6-(tert-butyl-diphenyl-silanyloxymethyl)-2-methyl-octanal (187862-57-3) → (4S,5S,6S,9R)-6-Benzyloxy-9-(tert-butyl-diphenyl-silanyloxymethyl)-2,5-dimethyl-undec-1-en-4-ol (187862-60-8)

Guidance literature:

With titanium tetrachloride; at -78 ℃; for 4h;

DOI:10.1016/S0040-4039(97)00096-8

Reference yield:

(R)-4-(tert-Butyl-diphenyl-silanyloxymethyl)-hexanal (187862-43-7) → (4S,5S,6S,9R)-6-Benzyloxy-9-(tert-butyl-diphenyl-silanyloxymethyl)-2,5-dimethyl-undec-1-en-4-ol (187862-60-8)

Guidance literature:

Multi-step reaction with 3 steps

1.1: 89 percent / TMSOTf / CH₂Cl₂ / 37 h / -78 - -55 °C

2.1: O₃ / pyridine / methanol / -78 °C

2.2: 89 percent / Me₂S / methanol / 12 h / -78 - 20 °C

3.1: 71 percent / TiCl₄ / CH₂Cl₂ / 1 h / -78 °C

With trimethylsilyl trifluoromethanesulfonate; titanium tetrachloride; ozone; pyridine; In methanol; dichloromethane;

DOI:10.1021/jo001767c

upstream raw materials:

dimethyl-(2-methyl-2-propenyl)phenylsilane

(2R,3S,6R)-3-Benzyloxy-6-(tert-butyl-diphenyl-silanyloxymethyl)-2-methyl-octanal

(E)-(R)-4-Hydroxymethyl-hex-2-enoic acid methyl ester

(R)-2-((tert-butyldimethylsilyloxy)methyl)butan-1-ol

Downstream raw materials:

rutamycin B

(4S,5R,6S,9R)-6-Benzyloxy-4-(tert-butyl-dimethyl-silanyloxy)-9-(tert-butyl-diphenyl-silanyloxymethyl)-5-methyl-undecan-2-one

(2R,4S,5S,10S,11R,12S,15R)-2,12-Bis-benzyloxy-4,10-bis-(tert-butyl-dimethyl-silanyloxy)-15-(tert-butyl-diphenyl-silanyloxymethyl)-5,11-dimethyl-heptadecan-8-one

N'-[(3S,4R,5S,8R)-5-Benzyloxy-1-[(3S,4S,6R)-6-benzyloxy-4-(tert-butyl-dimethyl-silanyloxy)-3-methyl-heptyl]-3-(tert-butyl-dimethyl-silanyloxy)-8-(tert-butyl-diphenyl-silanyloxymethyl)-4-methyl-dec-(E)-ylidene]-N,N-dimethyl-hydrazine