(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

Base Information

Chemical Name:(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
CAS No.:164215-50-3
Molecular Formula:C₃₃H₄₄O₁₂
Molecular Weight:632.705
Hs Code.:

(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

Synonyms:(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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Chemical Property of (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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Technology Process of (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

There total 23 articles about (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 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%

: 164215-49-0
(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

: 164215-50-3
(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

Guidance literature:: With Dess-Martin periodane;
DOI:10.1021/ja00102a074

Reference yield:

: 164215-43-4
(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

: 164215-50-3
(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

Guidance literature:: Multi-step reaction with 8 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

5: aq. NaClO₂ / 2-methyl-propan-2-ol; various solvent(s) / 3 h / 10 °C

6: CH₂Cl₂ / 22 h

7: 90 percent / HF*pyridine / tetrahydrofuran

8: 84 percent / Dess-Martin periodinane, pyridine / CH₂Cl₂ / 0.58 h / 23 °C

With pyridine; dichloro-acetic acid; dmap; sodium chlorite; hydrogen; Dess-Martin periodane; pyridine hydrogenfluoride; palladium on activated charcoal; In tetrahydrofuran; pyridine; methanol; dichloromethane; tert-butyl alcohol;
DOI:10.1021/ja00136a008

Reference yield:

: 164215-45-6
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

: 164215-50-3
(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

Guidance literature:: Multi-step reaction with 6 steps

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

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

3: aq. NaClO₂ / 2-methyl-propan-2-ol; various solvent(s) / 3 h / 10 °C

4: CH₂Cl₂ / 22 h

5: 90 percent / HF*pyridine / tetrahydrofuran

6: 84 percent / Dess-Martin periodinane, pyridine / CH₂Cl₂ / 0.58 h / 23 °C

With pyridine; sodium chlorite; hydrogen; Dess-Martin periodane; pyridine hydrogenfluoride; palladium on activated charcoal; In tetrahydrofuran; pyridine; dichloromethane; tert-butyl alcohol;
DOI:10.1021/ja00136a008