Benzoic acid (2R,3R,5R,7S,8R,9R)-7-[2-(tert-butyl-dimethyl-silanyloxy)-ethyl]-2-((1S,3S,4R)-3-hydroxy-1-methoxy-4-methyl-hex-5-enyl)-3-(2-methoxy-ethoxymethoxy)-4,4,8-trimethyl-1,6-dioxa-spiro[4.5]dec-9-yl ester

Base Information

• Chemical Name: Benzoic acid (2R,3R,5R,7S,8R,9R)-7-[2-(tert-butyl-dimethyl-silanyloxy)-ethyl]-2-((1S,3S,4R)-3-hydroxy-1-methoxy-4-methyl-hex-5-enyl)-3-(2-methoxy-ethoxymethoxy)-4,4,8-trimethyl-1,6-dioxa-spiro[4.5]dec-9-yl ester
• CAS No.: 219317-95-0
• Molecular Formula: C₃₈H₆₄O₁₀Si
• Molecular Weight: 709.006

Synonyms:Benzoic acid (2R,3R,5R,7S,8R,9R)-7-[2-(tert-butyl-dimethyl-silanyloxy)-ethyl]-2-((1S,3S,4R)-3-hydroxy-1-methoxy-4-methyl-hex-5-enyl)-3-(2-methoxy-ethoxymethoxy)-4,4,8-trimethyl-1,6-dioxa-spiro[4.5]dec-9-yl ester

Chemical Property of Benzoic acid (2R,3R,5R,7S,8R,9R)-7-[2-(tert-butyl-dimethyl-silanyloxy)-ethyl]-2-((1S,3S,4R)-3-hydroxy-1-methoxy-4-methyl-hex-5-enyl)-3-(2-methoxy-ethoxymethoxy)-4,4,8-trimethyl-1,6-dioxa-spiro[4.5]dec-9-yl ester

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Technology Process of Benzoic acid (2R,3R,5R,7S,8R,9R)-7-[2-(tert-butyl-dimethyl-silanyloxy)-ethyl]-2-((1S,3S,4R)-3-hydroxy-1-methoxy-4-methyl-hex-5-enyl)-3-(2-methoxy-ethoxymethoxy)-4,4,8-trimethyl-1,6-dioxa-spiro[4.5]dec-9-yl ester

There total 5 articles about Benzoic acid (2R,3R,5R,7S,8R,9R)-7-[2-(tert-butyl-dimethyl-silanyloxy)-ethyl]-2-((1S,3S,4R)-3-hydroxy-1-methoxy-4-methyl-hex-5-enyl)-3-(2-methoxy-ethoxymethoxy)-4,4,8-trimethyl-1,6-dioxa-spiro[4.5]dec-9-yl 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:

t-butyldimethylsiyl triflate (69739-34-0) → Benzoic acid (2R,3R,5R,7S,8R,9R)-7-[2-(tert-butyl-dimethyl-silanyloxy)-ethyl]-2-((1S,3S,4R)-3-hydroxy-1-methoxy-4-methyl-hex-5-enyl)-3-(2-methoxy-ethoxymethoxy)-4,4,8-trimethyl-1,6-dioxa-spiro[4.5]dec-9-yl ester (219317-95-0)

Guidance literature:

Multi-step reaction with 3 steps

1: 2,6-lutidine / CH₂Cl₂ / 0.17 h / 0 °C

2: 1.) O₃, 2.) Bu₃P / 1.) CH₂Cl₂, -78 deg C, 2.) CH₂Cl₂, from -78 deg C to RT, 10 h

With 2,6-dimethylpyridine; tributylphosphine; ozone; In dichloromethane;

DOI:10.1021/ja980836q

Reference yield:

Benzoic acid (2R,3R,5R,7S,8R,9R)-7-(2-hydroxy-ethyl)-2-((S)-1-methoxy-but-3-enyl)-3-(2-methoxy-ethoxymethoxy)-4,4,8-trimethyl-1,6-dioxa-spiro[4.5]dec-9-yl ester (219317-90-5) → Benzoic acid (2R,3R,5R,7S,8R,9R)-7-[2-(tert-butyl-dimethyl-silanyloxy)-ethyl]-2-((1S,3S,4R)-3-hydroxy-1-methoxy-4-methyl-hex-5-enyl)-3-(2-methoxy-ethoxymethoxy)-4,4,8-trimethyl-1,6-dioxa-spiro[4.5]dec-9-yl ester (219317-95-0)

Guidance literature:

Multi-step reaction with 3 steps

1: 2,6-lutidine / CH₂Cl₂ / 0.17 h / 0 °C

2: 1.) O₃, 2.) Bu₃P / 1.) CH₂Cl₂, -78 deg C, 2.) CH₂Cl₂, from -78 deg C to RT, 10 h

With 2,6-dimethylpyridine; tributylphosphine; ozone; In dichloromethane;

DOI:10.1021/ja980836q

Reference yield:

Benzoic acid (2R,3R,5R,7S,8R,9R)-7-[2-(tert-butyl-phenyl-silanyloxy)-ethyl]-2-((S)-1-methoxy-but-3-enyl)-3-(2-methoxy-ethoxymethoxy)-4,4,8-trimethyl-1,6-dioxa-spiro[4.5]dec-9-yl ester → Benzoic acid (2R,3R,5R,7S,8R,9R)-7-[2-(tert-butyl-dimethyl-silanyloxy)-ethyl]-2-((1S,3S,4R)-3-hydroxy-1-methoxy-4-methyl-hex-5-enyl)-3-(2-methoxy-ethoxymethoxy)-4,4,8-trimethyl-1,6-dioxa-spiro[4.5]dec-9-yl ester (219317-95-0)

Guidance literature:

Multi-step reaction with 4 steps

1: 97 percent / TBAF / tetrahydrofuran / 2.5 h

2: 2,6-lutidine / CH₂Cl₂ / 0.17 h / 0 °C

3: 1.) O₃, 2.) Bu₃P / 1.) CH₂Cl₂, -78 deg C, 2.) CH₂Cl₂, from -78 deg C to RT, 10 h

With 2,6-dimethylpyridine; tributylphosphine; tetrabutyl ammonium fluoride; ozone; In tetrahydrofuran; dichloromethane;

DOI:10.1021/ja980836q

upstream raw materials:

trans-2-Butene

t-butyldimethylsiyl triflate

Benzoic acid (2R,3R,5R,7S,8R,9R)-7-(2-hydroxy-ethyl)-2-((S)-1-methoxy-but-3-enyl)-3-(2-methoxy-ethoxymethoxy)-4,4,8-trimethyl-1,6-dioxa-spiro[4.5]dec-9-yl ester

Benzoic acid (2R,3R,5R,7S,8R,9R)-7-[2-(tert-butyl-dimethyl-silanyloxy)-ethyl]-2-((S)-1-methoxy-but-3-enyl)-3-(2-methoxy-ethoxymethoxy)-4,4,8-trimethyl-1,6-dioxa-spiro[4.5]dec-9-yl ester

Downstream raw materials:

(2R,2(1S,3S,4S,5S,6S),3R,5R,7S,8R,9R)-9-benzoyloxy-7-(2-tert-butyldimethylsiloxyethyl)-2-(5-hydroxy-1-methoxy-4,6-dimethyl-3-benzoyloxy-8-nonenyl)-3-(2-methoxyethoxymethyl)oxy-4,4,8-trimethyl-1,6-dioxaspiro[4.5]decane

(2R,2(1S,3S,4S,5R,6R),3R,5R,7S,8R,9R)-9-benzoyloxy-7-(2-tert-butyldimethylsiloxyethyl)-2-(5-hydroxy-1-methoxy-4,6-dimethyl-3-benzoyloxy-8-nonenyl)-3-(2-methoxyethoxymethyl)oxy-4,4,8-trimethyl-1,6-dioxaspiro[4.5]decane

(2R,2(1S,3S,4S),3R,5R,7S,8R,9R)-9-benzoyloxy-7-(2-tert-butyldimethylsiloxyethyl)-2-(3-benzoyloxy-1-methoxy-4-methyl-5-hexenyl)-3-(2-methoxyethoxymethyl)oxy-4,4,8-trimethyl-1,6-dioxaspiro[4.5]decane

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