(2S,3S,6R,8R,11S)-3,11-bis(benzyloxy)-2,8-dimethyl-1,7-dioxaspiro[5.5]undecan-4-one

Base Information

Chemical Name:(2S,3S,6R,8R,11S)-3,11-bis(benzyloxy)-2,8-dimethyl-1,7-dioxaspiro[5.5]undecan-4-one
CAS No.:1407163-81-8
Molecular Formula:C₂₅H₃₀O₅
Molecular Weight:410.51
Hs Code.:

Synonyms:(2S,3S,6R,8R,11S)-3,11-bis(benzyloxy)-2,8-dimethyl-1,7-dioxaspiro[5.5]undecan-4-one

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Chemical Property of (2S,3S,6R,8R,11S)-3,11-bis(benzyloxy)-2,8-dimethyl-1,7-dioxaspiro[5.5]undecan-4-one

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Technology Process of (2S,3S,6R,8R,11S)-3,11-bis(benzyloxy)-2,8-dimethyl-1,7-dioxaspiro[5.5]undecan-4-one

There total 31 articles about (2S,3S,6R,8R,11S)-3,11-bis(benzyloxy)-2,8-dimethyl-1,7-dioxaspiro[5.5]undecan-4-one 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: 79.0%

: 1407163-66-9
(5S,6S,10S,13R)-6,10-bis(benzyloxy)-2,2,3,3,5,13,15,15,16,16-decamethyl-4,14-dioxa-3,15-disilaheptadec-8-yn-7-one

: 1407163-81-8
(2S,3S,6R,8R,11S)-3,11-bis(benzyloxy)-2,8-dimethyl-1,7-dioxaspiro[5.5]undecan-4-one

Guidance literature:: (5S,6S,10S,13R)-6,10-bis(benzyloxy)-2,2,3,3,5,13,15,15,16,16-decamethyl-4,14-dioxa-3,15-disilaheptadec-8-yn-7-one; With camphor-10-sulfonic acid; In methanol; at 0 - 20 ℃; for 2h;

With toluene-4-sulfonic acid; In toluene; at 20 ℃; for 24h;
DOI:10.1039/c2ob26396c

Reference yield:

: 1437598-89-4
(2S,3S,7S,10R)-3,7-bis(benzyloxy)-2,10-dihydroxyundec-5-yn-4-one

: 1407163-81-8
(2S,3S,6R,8R,11S)-3,11-bis(benzyloxy)-2,8-dimethyl-1,7-dioxaspiro[5.5]undecan-4-one

: 1407163-82-9
(2S,3S,6S,8R,11S)-3,11-bis(benzyloxy)-2,8-dimethyl-1,7-dioxaspiro[5.5]undecan-4-one

Guidance literature:: With toluene-4-sulfonic acid; In water; toluene; at 20 ℃; for 12h; Overall yield = 89 %; Inert atmosphere;
DOI:10.1002/ejoc.201201246

Reference yield:

: 1407163-68-1
((2R,5S)-5-(benzyloxy)hept-6-yn-2-yloxy)(tert-butyl)dimethylsilane

: 1407163-81-8
(2S,3S,6R,8R,11S)-3,11-bis(benzyloxy)-2,8-dimethyl-1,7-dioxaspiro[5.5]undecan-4-one

Guidance literature:: Multi-step reaction with 3 steps

1.1: n-butyllithium / tetrahydrofuran; hexane / 1 h / -78 °C

1.2: 1 h / -78 °C

2.1: Dess-Martin periodane / dichloromethane / 1 h / 0 °C

3.1: camphor-10-sulfonic acid / methanol / 2 h / 0 - 20 °C

3.2: 24 h / 20 °C

With n-butyllithium; camphor-10-sulfonic acid; Dess-Martin periodane; In tetrahydrofuran; methanol; hexane; dichloromethane;
DOI:10.1039/c2ob26396c