(2R,3S,5R)-5-tert-butyldiphenylsilyloxymethyl-2-propenyl-2,3-methano-1-tert-butyloxycarbonylpyrrolidine

Base Information

• Chemical Name: (2R,3S,5R)-5-tert-butyldiphenylsilyloxymethyl-2-propenyl-2,3-methano-1-tert-butyloxycarbonylpyrrolidine
• CAS No.: 433715-82-3
• Molecular Formula: C₃₀H₄₁NO₃Si
• Molecular Weight: 491.746
• Mol file: 433715-82-3.mol

Synonyms:(2R,3S,5R)-5-tert-butyldiphenylsilyloxymethyl-2-propenyl-2,3-methano-1-tert-butyloxycarbonylpyrrolidine

Chemical Property of (2R,3S,5R)-5-tert-butyldiphenylsilyloxymethyl-2-propenyl-2,3-methano-1-tert-butyloxycarbonylpyrrolidine

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2R,3S,5R)-5-tert-butyldiphenylsilyloxymethyl-2-propenyl-2,3-methano-1-tert-butyloxycarbonylpyrrolidine

There total 1 articles about (2R,3S,5R)-5-tert-butyldiphenylsilyloxymethyl-2-propenyl-2,3-methano-1-tert-butyloxycarbonylpyrrolidine 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: 30.0%

(3R,5R)-5-tert-butyldiphenylsilyloxymethyl-3-trimethylstannylmethyl-1-tert-butyloxycarbonylpyrrolidin-2-one + allylmagnesium bromide (1730-25-2) → (2R,3S,5R)-5-tert-butyldiphenylsilyloxymethyl-2-propenyl-2,3-methano-1-tert-butyloxycarbonylpyrrolidine (433715-82-3)

Guidance literature:

(3R,5R)-5-tert-butyldiphenylsilyloxymethyl-3-trimethylstannylmethyl-1-tert-butyloxycarbonylpyrrolidin-2-one; allylmagnesium bromide; In tetrahydrofuran; diethyl ether; at -78 ℃; for 1.5h;

With trifluoroacetic acid; In dichloromethane; at 0 ℃; for 0.166667h; Further stages.;

DOI:10.1021/jo0111715

Reference yield: 85.0%

(2R,3S,5R)-5-tert-butyldiphenylsilyloxymethyl-2-propenyl-2,3-methano-1-tert-butyloxycarbonylpyrrolidine (433715-82-3) → 3-(tert-butyl-diphenyl-silanyloxymethyl)-1-formyl-2-aza-bicyclo[3.1.0]hexane-2-carboxylic acid tert-butyl ester (433716-00-8)

Guidance literature:

(2R,3S,5R)-5-tert-butyldiphenylsilyloxymethyl-2-propenyl-2,3-methano-1-tert-butyloxycarbonylpyrrolidine; With ozone; In dichloromethane; at -78 ℃; for 0.166667h;

With dimethylsulfide; In dichloromethane; at -78 - 20 ℃; Further stages.;

DOI:10.1021/jo0111715

Reference yield:

(2R,3S,5R)-5-tert-butyldiphenylsilyloxymethyl-2-propenyl-2,3-methano-1-tert-butyloxycarbonylpyrrolidine (433715-82-3) → 3-(tert-butyl-diphenyl-silanyloxymethyl)-hexahydro-3a-aza-cyclopropa[c]pentalen-4-one

Guidance literature:

Multi-step reaction with 6 steps

1.1: O₃ / CH₂Cl₂ / 0.17 h / -78 °C

1.2: 85 percent / Me₂S / CH₂Cl₂ / -78 - 20 °C

2.1: benzene / 30 h / Heating

3.1: H₂ / 10percent Pd/C / ethanol / 20 °C / 760.05 Torr

4.1: trifluoroacetic acid / CH₂Cl₂ / 0 °C

5.1: LiOH / tetrahydrofuran; H₂O / 0 - 20 °C

6.1: diisopropylethylamine; bis(2-oxo-3-oxazolidinyl)phosphinic chloride / CH₂Cl₂ / -10 - 20 °C

With lithium hydroxide; hydrogen; bis-(2-oxo-3-oxazolidinyl)phosphoryl chloride; ozone; N-ethyl-N,N-diisopropylamine; trifluoroacetic acid; 10percent Pd/C; In tetrahydrofuran; ethanol; dichloromethane; water; benzene;

DOI:10.1021/jo0111715

upstream raw materials:

allylmagnesium bromide

Downstream raw materials:

3-(tert-butyl-diphenyl-silanyloxymethyl)-1-formyl-2-aza-bicyclo[3.1.0]hexane-2-carboxylic acid tert-butyl ester

(2R,3S,5R)-5-tert-butyldiphenylsilyloxymethyl-2-(2-methoxycarbonylvinyl)-2,3-methano-1-tert-butyloxycarbonylpyrrolidine