Benzoic acid (2R,3R,5R,7S,8R,9R)-7-[2-(tert-butyl-diphenyl-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-diphenyl-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.:180590-86-7
Molecular Formula:C₄₈H₆₈O₁₀Si
Molecular Weight:833.147
Hs Code.:

Benzoic acid (2R,3R,5R,7S,8R,9R)-7-[2-(tert-butyl-diphenyl-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

Synonyms:Benzoic acid (2R,3R,5R,7S,8R,9R)-7-[2-(tert-butyl-diphenyl-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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Chemical Property of Benzoic acid (2R,3R,5R,7S,8R,9R)-7-[2-(tert-butyl-diphenyl-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-diphenyl-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 7 articles about Benzoic acid (2R,3R,5R,7S,8R,9R)-7-[2-(tert-butyl-diphenyl-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:

: 180590-83-4
Benzoic acid (2S,3R,5R,7S,8R,9R)-2-but-3-enoyl-7-[2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-3-(2-methoxy-ethoxymethoxy)-4,4,8-trimethyl-1,6-dioxa-spiro[4.5]dec-9-yl ester

: 180590-86-7
Benzoic acid (2R,3R,5R,7S,8R,9R)-7-[2-(tert-butyl-diphenyl-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

Guidance literature:: Multi-step reaction with 4 steps

1: 85 percent / LiBH₄ / tetrahydrofuran / 1 h / -10 °C

2: 1.) 18-crown-6, potassium hydride / 1) THF, 0 deg C, 5 min; 2) THF, 25 deg C, 12 h

3: 1.) O₃, 2.) Me₂S / 1) CH₃OH, CH₂Cl₂, -78 deg C; 2) CH₂Cl₂, CH₃OH, 25 deg C, 12 h

4: 1.) potassium tert-butoxide, n-BuLi, 2.) (+)-B-methoxydiisopinocampheylborane, 3.) BF₃*Et₂O

With (+)-Ipc₂BOMe; lithium borohydride; n-butyllithium; 18-crown-6 ether; dimethylsulfide; boron trifluoride diethyl etherate; potassium tert-butylate; potassium hydride; ozone; In tetrahydrofuran;
DOI:10.1021/jo960314y

Reference yield:

: 180590-81-2
Benzoic acid (2S,3R,5R,7S,8R,9R)-7-[2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-2-formyl-3-(2-methoxy-ethoxymethoxy)-4,4,8-trimethyl-1,6-dioxa-spiro[4.5]dec-9-yl ester

: 180590-86-7
Benzoic acid (2R,3R,5R,7S,8R,9R)-7-[2-(tert-butyl-diphenyl-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

Guidance literature:: Multi-step reaction with 6 steps

1: 88.8 percent / ZnCl₂ / tetrahydrofuran; CH₂Cl₂ / 0.25 h / -78 °C

2: 1.) oxalyl chloride, DMSO, 2.) Et₃N / 1) CH₂Cl₂, -40 deg C, 10 min; 2) CH₂Cl₂, -78 deg C --> rt

3: 85 percent / LiBH₄ / tetrahydrofuran / 1 h / -10 °C

4: 1.) 18-crown-6, potassium hydride / 1) THF, 0 deg C, 5 min; 2) THF, 25 deg C, 12 h

5: 1.) O₃, 2.) Me₂S / 1) CH₃OH, CH₂Cl₂, -78 deg C; 2) CH₂Cl₂, CH₃OH, 25 deg C, 12 h

6: 1.) potassium tert-butoxide, n-BuLi, 2.) (+)-B-methoxydiisopinocampheylborane, 3.) BF₃*Et₂O

With (+)-Ipc₂BOMe; lithium borohydride; n-butyllithium; oxalyl dichloride; 18-crown-6 ether; dimethylsulfide; boron trifluoride diethyl etherate; potassium tert-butylate; potassium hydride; ozone; dimethyl sulfoxide; triethylamine; zinc(II) chloride; In tetrahydrofuran; dichloromethane;
DOI:10.1021/jo960314y

Reference yield:

: 180590-80-1
Benzoic acid (2R,3R,5R,7S,8R,9R)-7-[2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-2-hydroxymethyl-3-(2-methoxy-ethoxymethoxy)-4,4,8-trimethyl-1,6-dioxa-spiro[4.5]dec-9-yl ester

: 180590-86-7
Benzoic acid (2R,3R,5R,7S,8R,9R)-7-[2-(tert-butyl-diphenyl-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

Guidance literature:: Multi-step reaction with 7 steps

1: 1.) oxalyl chloride, DMSO, 2.) Et₃N / 1) CH₂Cl₂, -40 deg C, 10 min; 2) CH₂Cl₂, -78 --> rt

2: 88.8 percent / ZnCl₂ / tetrahydrofuran; CH₂Cl₂ / 0.25 h / -78 °C

3: 1.) oxalyl chloride, DMSO, 2.) Et₃N / 1) CH₂Cl₂, -40 deg C, 10 min; 2) CH₂Cl₂, -78 deg C --> rt

4: 85 percent / LiBH₄ / tetrahydrofuran / 1 h / -10 °C

5: 1.) 18-crown-6, potassium hydride / 1) THF, 0 deg C, 5 min; 2) THF, 25 deg C, 12 h

6: 1.) O₃, 2.) Me₂S / 1) CH₃OH, CH₂Cl₂, -78 deg C; 2) CH₂Cl₂, CH₃OH, 25 deg C, 12 h

7: 1.) potassium tert-butoxide, n-BuLi, 2.) (+)-B-methoxydiisopinocampheylborane, 3.) BF₃*Et₂O

With (+)-Ipc₂BOMe; lithium borohydride; n-butyllithium; oxalyl dichloride; 18-crown-6 ether; dimethylsulfide; boron trifluoride diethyl etherate; potassium tert-butylate; potassium hydride; ozone; dimethyl sulfoxide; triethylamine; zinc(II) chloride; In tetrahydrofuran; dichloromethane;
DOI:10.1021/jo960314y