(1S,3S,4R,5S)-5-Acetoxy-3-[(R)-2-(tert-butyl-dimethyl-silanyloxy)-1-(tert-butyl-diphenyl-silanyloxy)-ethyl]-2,7-dioxa-bicyclo[2.2.1]heptane-1-carboxylic acid ethyl ester

Base Information

• Chemical Name: (1S,3S,4R,5S)-5-Acetoxy-3-[(R)-2-(tert-butyl-dimethyl-silanyloxy)-1-(tert-butyl-diphenyl-silanyloxy)-ethyl]-2,7-dioxa-bicyclo[2.2.1]heptane-1-carboxylic acid ethyl ester
• CAS No.: 539827-80-0
• Molecular Formula: C₃₄H₅₀O₈Si₂
• Molecular Weight: 642.937
• Mol file: 539827-80-0.mol

Synonyms:(1S,3S,4R,5S)-5-Acetoxy-3-[(R)-2-(tert-butyl-dimethyl-silanyloxy)-1-(tert-butyl-diphenyl-silanyloxy)-ethyl]-2,7-dioxa-bicyclo[2.2.1]heptane-1-carboxylic acid ethyl ester

Chemical Property of (1S,3S,4R,5S)-5-Acetoxy-3-[(R)-2-(tert-butyl-dimethyl-silanyloxy)-1-(tert-butyl-diphenyl-silanyloxy)-ethyl]-2,7-dioxa-bicyclo[2.2.1]heptane-1-carboxylic acid ethyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1S,3S,4R,5S)-5-Acetoxy-3-[(R)-2-(tert-butyl-dimethyl-silanyloxy)-1-(tert-butyl-diphenyl-silanyloxy)-ethyl]-2,7-dioxa-bicyclo[2.2.1]heptane-1-carboxylic acid ethyl ester

There total 1 articles about (1S,3S,4R,5S)-5-Acetoxy-3-[(R)-2-(tert-butyl-dimethyl-silanyloxy)-1-(tert-butyl-diphenyl-silanyloxy)-ethyl]-2,7-dioxa-bicyclo[2.2.1]heptane-1-carboxylic acid ethyl 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: 94.0%

acetic anhydride (108-24-7) + (1S,3S,4R,5S)-3-[(R)-2-(tert-Butyl-dimethyl-silanyloxy)-1-(tert-butyl-diphenyl-silanyloxy)-ethyl]-5-hydroxy-2,7-dioxa-bicyclo[2.2.1]heptane-1-carboxylic acid ethyl ester (539827-79-7) → (1S,3S,4R,5S)-5-Acetoxy-3-[(R)-2-(tert-butyl-dimethyl-silanyloxy)-1-(tert-butyl-diphenyl-silanyloxy)-ethyl]-2,7-dioxa-bicyclo[2.2.1]heptane-1-carboxylic acid ethyl ester (539827-80-0)

Guidance literature:

With dmap; triethylamine; In dichloromethane; at 20 ℃; for 5h;

DOI:10.1002/ejoc.200390108

Reference yield: 100.0%

(1S,3S,4R,5S)-5-Acetoxy-3-[(R)-2-(tert-butyl-dimethyl-silanyloxy)-1-(tert-butyl-diphenyl-silanyloxy)-ethyl]-2,7-dioxa-bicyclo[2.2.1]heptane-1-carboxylic acid ethyl ester (539827-80-0) → (1S,3S,4R,5S)-5-Acetoxy-3-[(R)-1-(tert-butyl-diphenyl-silanyloxy)-2-hydroxy-ethyl]-2,7-dioxa-bicyclo[2.2.1]heptane-1-carboxylic acid ethyl ester (539827-81-1)

Guidance literature:

With boron trifluoride diethyl etherate; In dichloromethane; at -30 - -3 ℃; for 1h;

DOI:10.1002/ejoc.200390108

Reference yield:

(1S,3S,4R,5S)-5-Acetoxy-3-[(R)-2-(tert-butyl-dimethyl-silanyloxy)-1-(tert-butyl-diphenyl-silanyloxy)-ethyl]-2,7-dioxa-bicyclo[2.2.1]heptane-1-carboxylic acid ethyl ester (539827-80-0) → (1S,3S,4R,5S)-5-Acetoxy-3-[(R)-2-(bis-benzyloxy-phosphoryloxy)-1-(tert-butyl-diphenyl-silanyloxy)-ethyl]-2,7-dioxa-bicyclo[2.2.1]heptane-1-carboxylic acid ethyl ester

Guidance literature:

Multi-step reaction with 2 steps

1.1: 100 percent / BF₃*Et₂O / CH₂Cl₂ / 1 h / -30 - -3 °C

2.1: tetrazole / CH₂Cl₂ / 20 °C

2.2: 72 percent / mCPBA / CH₂Cl₂ / 1 h / 0 °C

With 1H-tetrazole; boron trifluoride diethyl etherate; In dichloromethane;

DOI:10.1002/ejoc.200390108

upstream raw materials:

acetic anhydride

(1S,3S,4R,5S)-3-[(R)-2-(tert-Butyl-dimethyl-silanyloxy)-1-(tert-butyl-diphenyl-silanyloxy)-ethyl]-5-hydroxy-2,7-dioxa-bicyclo[2.2.1]heptane-1-carboxylic acid ethyl ester

Downstream raw materials:

(1S,3S,4R,5S)-5-Acetoxy-3-[(R)-1-(tert-butyl-diphenyl-silanyloxy)-2-hydroxy-ethyl]-2,7-dioxa-bicyclo[2.2.1]heptane-1-carboxylic acid ethyl ester