(5R,6S,9R,10S)-6-[3-(tert-Butyl-dimethyl-silanyloxy)-propyl]-8-(tert-butyl-diphenyl-silanyloxymethyl)-10-hydroxy-6,9-dimethyl-1,3-dioxa-spiro[4.5]dec-7-en-2-one

Base Information

• Chemical Name: (5R,6S,9R,10S)-6-[3-(tert-Butyl-dimethyl-silanyloxy)-propyl]-8-(tert-butyl-diphenyl-silanyloxymethyl)-10-hydroxy-6,9-dimethyl-1,3-dioxa-spiro[4.5]dec-7-en-2-one
• CAS No.: 912542-26-8
• Molecular Formula: C₃₆H₅₄O₆Si₂
• Molecular Weight: 638.992

Synonyms:(5R,6S,9R,10S)-6-[3-(tert-Butyl-dimethyl-silanyloxy)-propyl]-8-(tert-butyl-diphenyl-silanyloxymethyl)-10-hydroxy-6,9-dimethyl-1,3-dioxa-spiro[4.5]dec-7-en-2-one

Chemical Property of (5R,6S,9R,10S)-6-[3-(tert-Butyl-dimethyl-silanyloxy)-propyl]-8-(tert-butyl-diphenyl-silanyloxymethyl)-10-hydroxy-6,9-dimethyl-1,3-dioxa-spiro[4.5]dec-7-en-2-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
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Useful:

Technology Process of (5R,6S,9R,10S)-6-[3-(tert-Butyl-dimethyl-silanyloxy)-propyl]-8-(tert-butyl-diphenyl-silanyloxymethyl)-10-hydroxy-6,9-dimethyl-1,3-dioxa-spiro[4.5]dec-7-en-2-one

There total 6 articles about (5R,6S,9R,10S)-6-[3-(tert-Butyl-dimethyl-silanyloxy)-propyl]-8-(tert-butyl-diphenyl-silanyloxymethyl)-10-hydroxy-6,9-dimethyl-1,3-dioxa-spiro[4.5]dec-7-en-2-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: 89.0%

phenyl-carbamic acid 2-[3-(tert-butyl-dimethyl-silanyloxy)-propyl]-4-(tert-butyl-diphenyl-silanyloxymethyl)-2,5-dimethyl-7-oxa-bicyclo[4.1.0]hept-3-en-1-ylmethyl ester (912542-25-7) → (5R,6S,9R,10S)-6-[3-(tert-Butyl-dimethyl-silanyloxy)-propyl]-8-(tert-butyl-diphenyl-silanyloxymethyl)-10-hydroxy-6,9-dimethyl-1,3-dioxa-spiro[4.5]dec-7-en-2-one (912542-26-8)

Guidance literature:

With boron trifluoride diethyl etherate; In dichloromethane; at 0 ℃; for 0.666667h;

DOI:10.1021/jo061059c

Reference yield:

6-[3-(tert-butyl-dimethyl-silanyloxy)-propyl]-4-(tert-butyl-diphenyl-silanyloxymethyl)-3,6-dimethyl-cyclohexa-1,4-dienecarbaldehyde (912542-41-7) → (5R,6S,9R,10S)-6-[3-(tert-Butyl-dimethyl-silanyloxy)-propyl]-8-(tert-butyl-diphenyl-silanyloxymethyl)-10-hydroxy-6,9-dimethyl-1,3-dioxa-spiro[4.5]dec-7-en-2-one (912542-26-8)

Guidance literature:

Multi-step reaction with 4 steps

1: 93 percent / DIBAL-H / CH₂Cl₂; toluene / 0.5 h / -78 °C

2: 96 percent / VO(acac)2; t-BuOOH / CH₂Cl₂; decane / 0 - 23 °C

3: 94 percent / Et₃N / CH₂Cl₂ / 1 h / 23 °C

4: 89 percent / BF₃*OEt₂ / CH₂Cl₂ / 0.67 h / 0 °C

With tert.-butylhydroperoxide; bis(acetylacetonate)oxovanadium; boron trifluoride diethyl etherate; diisobutylaluminium hydride; triethylamine; In decane; dichloromethane; toluene;

DOI:10.1021/jo061059c

Reference yield:

[6-[3-(tert-butyl-dimethyl-silanyloxy)-propyl]-4-(tert-butyl-diphenyl-silanyloxymethyl)-3,6-dimethyl-cyclohexa-1,4-dienyl]-methanol (912542-24-6) → (5R,6S,9R,10S)-6-[3-(tert-Butyl-dimethyl-silanyloxy)-propyl]-8-(tert-butyl-diphenyl-silanyloxymethyl)-10-hydroxy-6,9-dimethyl-1,3-dioxa-spiro[4.5]dec-7-en-2-one (912542-26-8)

Guidance literature:

Multi-step reaction with 3 steps

1: 96 percent / VO(acac)2; t-BuOOH / CH₂Cl₂; decane / 0 - 23 °C

2: 94 percent / Et₃N / CH₂Cl₂ / 1 h / 23 °C

3: 89 percent / BF₃*OEt₂ / CH₂Cl₂ / 0.67 h / 0 °C

With tert.-butylhydroperoxide; bis(acetylacetonate)oxovanadium; boron trifluoride diethyl etherate; triethylamine; In decane; dichloromethane;

DOI:10.1021/jo061059c

upstream raw materials:

phenyl-carbamic acid 2-[3-(tert-butyl-dimethyl-silanyloxy)-propyl]-4-(tert-butyl-diphenyl-silanyloxymethyl)-2,5-dimethyl-7-oxa-bicyclo[4.1.0]hept-3-en-1-ylmethyl ester

6-[3-(tert-butyl-dimethyl-silanyloxy)-propyl]-4-(tert-butyl-diphenyl-silanyloxymethyl)-3,6-dimethyl-cyclohexa-1,4-dienecarbaldehyde

[6-[3-(tert-butyl-dimethyl-silanyloxy)-propyl]-4-(tert-butyl-diphenyl-silanyloxymethyl)-3,6-dimethyl-cyclohexa-1,4-dienyl]-methanol

[2-[3-(tert-butyl-dimethyl-silanyloxy)-propyl]-4-(tert-butyl-diphenyl-silanyloxymethyl)-2,5-dimethyl-7-oxa-bicyclo[4.1.0]hept-3-en-1-yl]-methanol

Downstream raw materials:

(1R,2S,5S)-4-(tert-Butyl-diphenyl-silanyloxymethyl)-1-hydroxy-2-(3-hydroxy-propyl)-2,5-dimethyl-cyclohex-3-enecarboxylic acid methyl ester

2-[3-(tert-butyl-dimethyl-silanyloxy)-propyl]-4-(tert-butyl-diphenyl-silanyloxymethyl)-1-hydroxymethyl-2,5-dimethyl-cyclohex-3-enol

6-[3-(tert-butyl-dimethyl-silanyloxy)-propyl]-8-(tert-butyl-diphenyl-silanyloxymethyl)-6,9-dimethyl-1,3-dioxa-spiro[4.5]dec-7-en-2-one

(1R,2S,5S)-2-[3-(tert-butyl-dimethyl-silanyloxy)-propyl]-4-(tert-butyl-diphenyl-silanyloxymethyl)-1-hydroxy-2,5-dimethyl-cyclohex-3-enecarbaldehyde

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