(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

Base Information

• Chemical Name: (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
• CAS No.: 539827-79-7
• Molecular Formula: C₃₂H₄₈O₇Si₂
• Molecular Weight: 600.9

Synonyms:(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

Chemical Property of (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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
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Useful:

Technology Process of (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

There total 1 articles about (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 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:

2-(trimethylsilyloxy)acrylic acid ethyl ester (98253-69-1) + 3-[2-(tert-butyl-dimethyl-silanyloxy)-1-(tert-butyl-diphenyl-silanyloxy)-ethyl]-oxirane-2-carbaldehyde (404829-96-5) → (1S,3S,4R,5R)-3-[(R)-1-(tert-Butyl-diphenyl-silanyloxy)-2-hydroxy-ethyl]-5-hydroxy-2,7-dioxa-bicyclo[2.2.1]heptane-1-carboxylic acid ethyl ester + (1S,3S,4R,5S)-3-[(R)-1-(tert-Butyl-diphenyl-silanyloxy)-2-hydroxy-ethyl]-5-hydroxy-2,7-dioxa-bicyclo[2.2.1]heptane-1-carboxylic acid ethyl ester + (1S,3S,4R,5R)-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 + (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)

Guidance literature:

With boron trifluoride diethyl etherate; In dichloromethane; at -45 ℃; for 6h;

DOI:10.1002/ejoc.200390108

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: 71.0%

tert-butylchlorodiphenylsilane (58479-61-1) + (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) → 3-[2-(tert-butyl-dimethyl-silanyloxy)-1-(tert-butyl-diphenyl-silanyloxy)-ethyl]-5-(tert-butyl-diphenyl-silanyloxy)-2,7-dioxa-bicyclo[2.2.1]heptane-1-carboxylic acid ethyl ester (539827-82-2)

Guidance literature:

With 1H-imidazole; In N,N-dimethyl-formamide; at 70 ℃; for 21h;

DOI:10.1002/ejoc.200390108

upstream raw materials:

2-(trimethylsilyloxy)acrylic acid ethyl ester

3-[2-(tert-butyl-dimethyl-silanyloxy)-1-(tert-butyl-diphenyl-silanyloxy)-ethyl]-oxirane-2-carbaldehyde

Downstream raw materials:

(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

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

(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

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

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