(2S,4S,6R,8S,10S)-2,8-bis-(2-benzyloxy-ethyl)-10-(tert-butyl-dimethyl-silanyloxy)-1,7-dioxa-spiro[5.5]undecan-4-ol

Base Information

• Chemical Name: (2S,4S,6R,8S,10S)-2,8-bis-(2-benzyloxy-ethyl)-10-(tert-butyl-dimethyl-silanyloxy)-1,7-dioxa-spiro[5.5]undecan-4-ol
• CAS No.: 185409-87-4
• Molecular Formula: C₃₃H₅₀O₆Si
• Molecular Weight: 570.842

Synonyms:(2S,4S,6R,8S,10S)-2,8-bis-(2-benzyloxy-ethyl)-10-(tert-butyl-dimethyl-silanyloxy)-1,7-dioxa-spiro[5.5]undecan-4-ol

Chemical Property of (2S,4S,6R,8S,10S)-2,8-bis-(2-benzyloxy-ethyl)-10-(tert-butyl-dimethyl-silanyloxy)-1,7-dioxa-spiro[5.5]undecan-4-ol

Chemical Property:

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Technology Process of (2S,4S,6R,8S,10S)-2,8-bis-(2-benzyloxy-ethyl)-10-(tert-butyl-dimethyl-silanyloxy)-1,7-dioxa-spiro[5.5]undecan-4-ol

There total 2 articles about (2S,4S,6R,8S,10S)-2,8-bis-(2-benzyloxy-ethyl)-10-(tert-butyl-dimethyl-silanyloxy)-1,7-dioxa-spiro[5.5]undecan-4-ol 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: 77.0%

1,13-dibenzyloxy-3,11-di(triethylsilyloxy)-5-tert-butyldimethylsilyloxy-9-hydroxy-tridecan-7-one (185409-83-0) → (2S,4S,6R,8S,10S)-2,8-bis-(2-benzyloxy-ethyl)-10-(tert-butyl-dimethyl-silanyloxy)-1,7-dioxa-spiro[5.5]undecan-4-ol (185409-87-4)

Guidance literature:

With pyridinium p-toluenesulfonate; In methanol; dichloromethane; at 20 ℃; for 3h;

DOI:10.1016/0040-4039(96)01961-2

Reference yield:

(3S,5S,11S)-1,13-bis-benzyloxy-3-(methoxypolystyrene-diisopropyl-silanyloxy)-5-(tert-butyl-dimethyl-silanyloxy)-9-hydroxy-11-triethylsilanyloxy-tridecan-7-one → (2S,4S,6R,8S,10S)-2,8-bis-(2-benzyloxy-ethyl)-10-(tert-butyl-dimethyl-silanyloxy)-1,7-dioxa-spiro[5.5]undecan-4-ol (185409-87-4)

Guidance literature:

(3S,5S,11S)-1,13-bis-benzyloxy-3-(methoxypolystyrene-diisopropyl-silanyloxy)-5-(tert-butyl-dimethyl-silanyloxy)-9-hydroxy-11-triethylsilanyloxy-tridecan-7-one; With pyridine; pyridine hydrogenfluoride; In tetrahydrofuran; at 20 ℃; for 1h;

With pyridinium p-toluenesulfonate; In methanol; dichloromethane; at 20 ℃; for 4h;

DOI:10.1039/b505746a

Reference yield: 93.8%

(2S,4S,6R,8S,10S)-2,8-bis-(2-benzyloxy-ethyl)-10-(tert-butyl-dimethyl-silanyloxy)-1,7-dioxa-spiro[5.5]undecan-4-ol (185409-87-4) → 1,13-dibenzyloxy-5,9-dihydroxy-spiroketal

Guidance literature:

With hydrogen fluoride; In water; acetonitrile; at 20 ℃; for 1.5h;

upstream raw materials:

1,13-dibenzyloxy-3,11-di(triethylsilyloxy)-5-tert-butyldimethylsilyloxy-9-hydroxy-tridecan-7-one

Downstream raw materials:

(2S,4S,6R,8S,10S)-2,8-Bis-(2-benzyloxy-ethyl)-10-(tert-butyl-dimethyl-silanyloxy)-4-methyl-1,7-dioxa-spiro[5.5]undecan-4-ol

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