Acetic acid (1S,3S,4S,5R,6R,7R)-7-acetoxy-1-((4R,5R)-4-acetoxy-5-methyl-6-phenyl-hexyl)-5-(tert-butyl-dimethyl-silanyloxymethyl)-3-formyl-4-hydroxy-4-vinyl-2,8-dioxa-bicyclo[3.2.1]oct-6-yl ester

Base Information

• Chemical Name: Acetic acid (1S,3S,4S,5R,6R,7R)-7-acetoxy-1-((4R,5R)-4-acetoxy-5-methyl-6-phenyl-hexyl)-5-(tert-butyl-dimethyl-silanyloxymethyl)-3-formyl-4-hydroxy-4-vinyl-2,8-dioxa-bicyclo[3.2.1]oct-6-yl ester
• CAS No.: 164215-47-8
• Molecular Formula: C₃₅H₅₂O₁₁Si
• Molecular Weight: 676.877

Synonyms:Acetic acid (1S,3S,4S,5R,6R,7R)-7-acetoxy-1-((4R,5R)-4-acetoxy-5-methyl-6-phenyl-hexyl)-5-(tert-butyl-dimethyl-silanyloxymethyl)-3-formyl-4-hydroxy-4-vinyl-2,8-dioxa-bicyclo[3.2.1]oct-6-yl ester

Chemical Property of Acetic acid (1S,3S,4S,5R,6R,7R)-7-acetoxy-1-((4R,5R)-4-acetoxy-5-methyl-6-phenyl-hexyl)-5-(tert-butyl-dimethyl-silanyloxymethyl)-3-formyl-4-hydroxy-4-vinyl-2,8-dioxa-bicyclo[3.2.1]oct-6-yl ester

Chemical Property:

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Technology Process of Acetic acid (1S,3S,4S,5R,6R,7R)-7-acetoxy-1-((4R,5R)-4-acetoxy-5-methyl-6-phenyl-hexyl)-5-(tert-butyl-dimethyl-silanyloxymethyl)-3-formyl-4-hydroxy-4-vinyl-2,8-dioxa-bicyclo[3.2.1]oct-6-yl ester

There total 19 articles about Acetic acid (1S,3S,4S,5R,6R,7R)-7-acetoxy-1-((4R,5R)-4-acetoxy-5-methyl-6-phenyl-hexyl)-5-(tert-butyl-dimethyl-silanyloxymethyl)-3-formyl-4-hydroxy-4-vinyl-2,8-dioxa-bicyclo[3.2.1]oct-6-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: 94.0%

Acetic acid (1S,3R,4S,5R,6R,7R)-7-acetoxy-1-((4R,5R)-4-acetoxy-5-methyl-6-phenyl-hexyl)-5-(tert-butyl-dimethyl-silanyloxymethyl)-4-hydroxy-3-hydroxymethyl-4-vinyl-2,8-dioxa-bicyclo[3.2.1]oct-6-yl ester (164215-46-7) → Acetic acid (1S,3S,4S,5R,6R,7R)-7-acetoxy-1-((4R,5R)-4-acetoxy-5-methyl-6-phenyl-hexyl)-5-(tert-butyl-dimethyl-silanyloxymethyl)-3-formyl-4-hydroxy-4-vinyl-2,8-dioxa-bicyclo[3.2.1]oct-6-yl ester (164215-47-8)

Guidance literature:

With Dess-Martin periodane;

DOI:10.1021/ja00102a074

Reference yield:

(1S,3R,4S,5R,6R,7R)-3,5-Bis-(tert-butyl-dimethyl-silanyloxymethyl)-4-ethynyl-1-((4R,5R)-4-hydroxy-5-methyl-6-phenyl-hexyl)-2,8-dioxa-bicyclo[3.2.1]octane-4,6,7-triol (164215-43-4) → Acetic acid (1S,3S,4S,5R,6R,7R)-7-acetoxy-1-((4R,5R)-4-acetoxy-5-methyl-6-phenyl-hexyl)-5-(tert-butyl-dimethyl-silanyloxymethyl)-3-formyl-4-hydroxy-4-vinyl-2,8-dioxa-bicyclo[3.2.1]oct-6-yl ester (164215-47-8)

Guidance literature:

Multi-step reaction with 4 steps

1: 94 percent / 4-DMAP / CH₂Cl₂ / 12 h

2: 90 percent / Cl₂CHCO₂H / methanol / 7 h

3: H₂ / 5percent Pd/C / pyridine / 2 h / 760 Torr

4: 94 percent / Dess-Martin periodinane / CH₂Cl₂ / 2 h / 23 °C

With dichloro-acetic acid; dmap; hydrogen; Dess-Martin periodane; palladium on activated charcoal; In pyridine; methanol; dichloromethane;

DOI:10.1021/ja00136a008

Reference yield:

Acetic acid (1S,3R,4S,5R,6R,7R)-7-acetoxy-1-((4R,5R)-4-acetoxy-5-methyl-6-phenyl-hexyl)-5-(tert-butyl-dimethyl-silanyloxymethyl)-4-ethynyl-4-hydroxy-3-hydroxymethyl-2,8-dioxa-bicyclo[3.2.1]oct-6-yl ester (164215-45-6) → Acetic acid (1S,3S,4S,5R,6R,7R)-7-acetoxy-1-((4R,5R)-4-acetoxy-5-methyl-6-phenyl-hexyl)-5-(tert-butyl-dimethyl-silanyloxymethyl)-3-formyl-4-hydroxy-4-vinyl-2,8-dioxa-bicyclo[3.2.1]oct-6-yl ester (164215-47-8)

Guidance literature:

Multi-step reaction with 2 steps

1: H₂ / 5percent Pd/C / pyridine / 2 h / 760 Torr

2: 94 percent / Dess-Martin periodinane / CH₂Cl₂ / 2 h / 23 °C

With hydrogen; Dess-Martin periodane; palladium on activated charcoal; In pyridine; dichloromethane;

DOI:10.1021/ja00136a008

upstream raw materials:

Acetic acid (1S,3R,4S,5R,6R,7R)-7-acetoxy-1-((4R,5R)-4-acetoxy-5-methyl-6-phenyl-hexyl)-5-(tert-butyl-dimethyl-silanyloxymethyl)-4-hydroxy-3-hydroxymethyl-4-vinyl-2,8-dioxa-bicyclo[3.2.1]oct-6-yl ester

(1S,3R,4S,5R,6R,7R)-3,5-Bis-(tert-butyl-dimethyl-silanyloxymethyl)-4-ethynyl-1-((4R,5R)-4-hydroxy-5-methyl-6-phenyl-hexyl)-2,8-dioxa-bicyclo[3.2.1]octane-4,6,7-triol

Acetic acid (1S,3R,4S,5R,6R,7R)-7-acetoxy-1-((4R,5R)-4-acetoxy-5-methyl-6-phenyl-hexyl)-5-(tert-butyl-dimethyl-silanyloxymethyl)-4-ethynyl-4-hydroxy-3-hydroxymethyl-2,8-dioxa-bicyclo[3.2.1]oct-6-yl ester

Acetic acid (1S,3R,4S,5R,6R,7R)-7-acetoxy-1-((4R,5R)-4-acetoxy-5-methyl-6-phenyl-hexyl)-3,5-bis-(tert-butyl-dimethyl-silanyloxymethyl)-4-ethynyl-4-hydroxy-2,8-dioxa-bicyclo[3.2.1]oct-6-yl ester

Downstream raw materials:

(1S,3S,4S,5R,6R,7R,4'R,5'R)-1-[4'-acetoxy-5'-methyl-6'-phenylhex-1'-yl]-3,4,5-tris(2,2-dimethylpropionyl)-4,6,7-trihydroxy-2,8-dioxabicyclo[3.2.1]octane

(+)-zaragozic acid

(1S,3S,4S,5R,6R,7R)-6,7-Diacetoxy-1-((4R,5R)-4-acetoxy-5-methyl-6-phenyl-hexyl)-4-hydroxy-5-hydroxymethyl-4-vinyl-2,8-dioxa-bicyclo[3.2.1]octane-3-carboxylic acid tert-butyl ester

(1S,3S,4S,5R,6R,7R)-6,7-Diacetoxy-1-((4R,5R)-4-acetoxy-5-methyl-6-phenyl-hexyl)-5-formyl-4-hydroxy-4-vinyl-2,8-dioxa-bicyclo[3.2.1]octane-3-carboxylic acid tert-butyl ester

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