[(1S,2S)-1-(tert-Butyl-diphenyl-silanyloxymethyl)-2-hydroxy-pent-4-enyl]-carbamic acid benzyl ester

Base Information

• Chemical Name: [(1S,2S)-1-(tert-Butyl-diphenyl-silanyloxymethyl)-2-hydroxy-pent-4-enyl]-carbamic acid benzyl ester
• CAS No.: 864973-85-3
• Molecular Formula: C₃₀H₃₇NO₄Si
• Molecular Weight: 503.714
• Mol file: 864973-85-3.mol

Synonyms:[(1S,2S)-1-(tert-Butyl-diphenyl-silanyloxymethyl)-2-hydroxy-pent-4-enyl]-carbamic acid benzyl ester

Chemical Property of [(1S,2S)-1-(tert-Butyl-diphenyl-silanyloxymethyl)-2-hydroxy-pent-4-enyl]-carbamic acid benzyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of [(1S,2S)-1-(tert-Butyl-diphenyl-silanyloxymethyl)-2-hydroxy-pent-4-enyl]-carbamic acid benzyl ester

There total 2 articles about [(1S,2S)-1-(tert-Butyl-diphenyl-silanyloxymethyl)-2-hydroxy-pent-4-enyl]-carbamic acid benzyl 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: 70.0%

N-(Benzyloxycarbonyl)-O-(tert-butyldiphenylsilyl)-L-serinal (122051-27-8) + allyl-trimethyl-silane (762-72-1) → [(1S,2S)-1-(tert-Butyl-diphenyl-silanyloxymethyl)-2-hydroxy-pent-4-enyl]-carbamic acid benzyl ester (864973-85-3)

Guidance literature:

With tin(IV) chloride; In toluene; at -78 ℃; for 4h;

DOI:10.1016/j.tetlet.2005.07.014

Reference yield:

methyl (2S)-3-(2,2-dimethyl-1,1-diphenyl-1-silapropoxy)-2-[(phenylmethoxy)carbonylamino]propanoate (135245-97-5) → [(1S,2S)-1-(tert-Butyl-diphenyl-silanyloxymethyl)-2-hydroxy-pent-4-enyl]-carbamic acid benzyl ester (864973-85-3)

Guidance literature:

Multi-step reaction with 2 steps

1: 80 percent / DIBAL-H / toluene / 6 h / -78 °C

2: 70 percent / SnCl₄ / toluene / 4 h / -78 °C

With tin(IV) chloride; diisobutylaluminium hydride; In toluene;

DOI:10.1016/j.tetlet.2005.07.014

Reference yield: 80.0%

[(1S,2S)-1-(tert-Butyl-diphenyl-silanyloxymethyl)-2-hydroxy-pent-4-enyl]-carbamic acid benzyl ester (864973-85-3) + 2,2-dimethoxy-propane (77-76-9) → (4S,5S)-5-Allyl-4-(tert-butyl-diphenyl-silanyloxymethyl)-2,2-dimethyl-oxazolidine-3-carboxylic acid benzyl ester (864973-86-4)

Guidance literature:

With 8-aminopyrene-1,3,6-trisulfonic acid, trisodium salt; In benzene; Heating;

DOI:10.1016/j.tetlet.2005.07.014

upstream raw materials:

N-(Benzyloxycarbonyl)-O-(tert-butyldiphenylsilyl)-L-serinal

allyl-trimethyl-silane

methyl (2S)-3-(2,2-dimethyl-1,1-diphenyl-1-silapropoxy)-2-[(phenylmethoxy)carbonylamino]propanoate

Downstream raw materials:

(4S,5S)-5-Allyl-4-(tert-butyl-diphenyl-silanyloxymethyl)-2,2-dimethyl-oxazolidine-3-carboxylic acid benzyl ester

(4S,5S)-5-Allyl-4-hydroxymethyl-2,2-dimethyl-oxazolidine-3-carboxylic acid benzyl ester

(4S,5S)-5-Allyl-4-azidomethyl-2,2-dimethyl-oxazolidine-3-carboxylic acid benzyl ester

(4S,5S)-5-Allyl-4-methanesulfonyloxymethyl-2,2-dimethyl-oxazolidine-3-carboxylic acid benzyl ester