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

Base Information

• Chemical Name: (1S,3S,4S,5S)-3-[(R)-2-(Bis-benzyloxy-phosphoryloxy)-1-(tert-butyl-diphenyl-silanyloxy)-ethyl]-5-(tert-butyl-diphenyl-silanyloxy)-2,7-dioxa-bicyclo[2.2.1]heptane-1-carboxylic acid ethyl ester
• CAS No.: 539827-84-4
• Molecular Formula: C₅₆H₆₅O₁₀PSi₂
• Molecular Weight: 985.271

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

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

Chemical Property:

Purity/Quality:

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

There total 4 articles about (1S,3S,4S,5S)-3-[(R)-2-(Bis-benzyloxy-phosphoryloxy)-1-(tert-butyl-diphenyl-silanyloxy)-ethyl]-5-(tert-butyl-diphenyl-silanyloxy)-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: 88.0%

Dibenzyl N,N-diisopropylphosphoramidite (108549-23-1) + (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 (539827-83-3) → (1S,3S,4S,5S)-3-[(R)-2-(Bis-benzyloxy-phosphoryloxy)-1-(tert-butyl-diphenyl-silanyloxy)-ethyl]-5-(tert-butyl-diphenyl-silanyloxy)-2,7-dioxa-bicyclo[2.2.1]heptane-1-carboxylic acid ethyl ester (539827-84-4)

Guidance literature:

Dibenzyl N,N-diisopropylphosphoramidite; (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; With 1H-tetrazole; In dichloromethane; at -10 ℃; for 1.5h;

With 3-chloro-benzenecarboperoxoic acid; In dichloromethane; at 0 ℃; for 1.08333h; Further stages.;

DOI:10.1002/ejoc.200390108

Reference yield:

tert-butylchlorodiphenylsilane (58479-61-1) → (1S,3S,4S,5S)-3-[(R)-2-(Bis-benzyloxy-phosphoryloxy)-1-(tert-butyl-diphenyl-silanyloxy)-ethyl]-5-(tert-butyl-diphenyl-silanyloxy)-2,7-dioxa-bicyclo[2.2.1]heptane-1-carboxylic acid ethyl ester (539827-84-4)

Guidance literature:

Multi-step reaction with 3 steps

1.1: 71 percent / imidazole / dimethylformamide / 21 h / 70 °C

2.1: 93 percent / BF₃*Et₂O / CH₂Cl₂ / 0.83 h / -20 - -5 °C

3.1: tetrazole / CH₂Cl₂ / 1.5 h / -10 °C

3.2: 88 percent / mCPBA / CH₂Cl₂ / 1.08 h / 0 °C

With 1H-imidazole; 1H-tetrazole; boron trifluoride diethyl etherate; In dichloromethane; N,N-dimethyl-formamide;

DOI:10.1002/ejoc.200390108

Reference yield:

(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,4S,5S)-3-[(R)-2-(Bis-benzyloxy-phosphoryloxy)-1-(tert-butyl-diphenyl-silanyloxy)-ethyl]-5-(tert-butyl-diphenyl-silanyloxy)-2,7-dioxa-bicyclo[2.2.1]heptane-1-carboxylic acid ethyl ester (539827-84-4)

Guidance literature:

Multi-step reaction with 3 steps

1.1: 71 percent / imidazole / dimethylformamide / 21 h / 70 °C

2.1: 93 percent / BF₃*Et₂O / CH₂Cl₂ / 0.83 h / -20 - -5 °C

3.1: tetrazole / CH₂Cl₂ / 1.5 h / -10 °C

3.2: 88 percent / mCPBA / CH₂Cl₂ / 1.08 h / 0 °C

With 1H-imidazole; 1H-tetrazole; boron trifluoride diethyl etherate; In dichloromethane; N,N-dimethyl-formamide;

DOI:10.1002/ejoc.200390108

upstream raw materials:

Dibenzyl N,N-diisopropylphosphoramidite

(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

tert-butylchlorodiphenylsilane

(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

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