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

Base Information

• Chemical Name: (2S,3S,6S,8R,11S)-3,11-bis(benzyloxy)-2,8-dimethyl-1,7-dioxaspiro[5.5]undecan-4-one
• CAS No.: 1407163-82-9
• Molecular Formula: C₂₅H₃₀O₅
• Molecular Weight: 410.51
• Mol file: 1407163-82-9.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 32 articles about (2S,3S,6S,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: 35.0%

(2S,3S,6R,8R,11S)-3,11-bis(benzyloxy)-2,8-dimethyl-1,7-dioxaspiro[5.5]undecan-4-one (1407163-81-8) → (2S,3S,6S,8R,11S)-3,11-bis(benzyloxy)-2,8-dimethyl-1,7-dioxaspiro[5.5]undecan-4-one (1407163-82-9)

Guidance literature:

With zinc dibromide; In dichloromethane; at 20 ℃; for 3h;

DOI:10.1039/c2ob26396c

Reference yield:

(2S,3S,7S,10R)-3,7-bis(benzyloxy)-2,10-dihydroxyundec-5-yn-4-one (1437598-89-4) → (2S,3S,6R,8R,11S)-3,11-bis(benzyloxy)-2,8-dimethyl-1,7-dioxaspiro[5.5]undecan-4-one (1407163-81-8) + (2S,3S,6S,8R,11S)-3,11-bis(benzyloxy)-2,8-dimethyl-1,7-dioxaspiro[5.5]undecan-4-one (1407163-82-9)

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:

((2R,5S)-5-(benzyloxy)hept-6-yn-2-yloxy)(tert-butyl)dimethylsilane (1407163-68-1) → (2S,3S,6S,8R,11S)-3,11-bis(benzyloxy)-2,8-dimethyl-1,7-dioxaspiro[5.5]undecan-4-one (1407163-82-9)

Guidance literature:

Multi-step reaction with 4 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

4.1: zinc dibromide / dichloromethane / 3 h / 20 °C

With n-butyllithium; camphor-10-sulfonic acid; Dess-Martin periodane; zinc dibromide; In tetrahydrofuran; methanol; hexane; dichloromethane;

DOI:10.1039/c2ob26396c

upstream raw materials:

(2S,5R)-2-(benzyloxy)-5-(tert-butyldimethylsilyloxy)hexan-1-ol

(2S,5R)-2-(benzyloxy)-5-(tert-butyldimethylsilyloxy)hexanal

((2R,5S)-5-(benzyloxy)-7,7-dibromohept-6-en-2-yloxy)(tert-butyl)dimethylsilane

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