(1S,3S,4S,5R,6R,7R)-1-((4S,5R)-4-Acetoxy-5-methyl-3-methylene-6-phenyl-hexyl)-6-cyclopropylcarbamoyloxy-4-hydroxy-7-(1-methoxy-1-methyl-ethoxy)-2,8-dioxa-bicyclo[3.2.1]octane-3,4,5-tricarboxylic acid tri-tert-butyl ester

Base Information

• Chemical Name: (1S,3S,4S,5R,6R,7R)-1-((4S,5R)-4-Acetoxy-5-methyl-3-methylene-6-phenyl-hexyl)-6-cyclopropylcarbamoyloxy-4-hydroxy-7-(1-methoxy-1-methyl-ethoxy)-2,8-dioxa-bicyclo[3.2.1]octane-3,4,5-tricarboxylic acid tri-tert-butyl ester
• CAS No.: 146008-75-5
• Molecular Formula: C₄₅H₆₇NO₁₅
• Molecular Weight: 862.025

Synonyms:

Chemical Property of (1S,3S,4S,5R,6R,7R)-1-((4S,5R)-4-Acetoxy-5-methyl-3-methylene-6-phenyl-hexyl)-6-cyclopropylcarbamoyloxy-4-hydroxy-7-(1-methoxy-1-methyl-ethoxy)-2,8-dioxa-bicyclo[3.2.1]octane-3,4,5-tricarboxylic acid tri-tert-butyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1S,3S,4S,5R,6R,7R)-1-((4S,5R)-4-Acetoxy-5-methyl-3-methylene-6-phenyl-hexyl)-6-cyclopropylcarbamoyloxy-4-hydroxy-7-(1-methoxy-1-methyl-ethoxy)-2,8-dioxa-bicyclo[3.2.1]octane-3,4,5-tricarboxylic acid tri-tert-butyl ester

There total 6 articles about (1S,3S,4S,5R,6R,7R)-1-((4S,5R)-4-Acetoxy-5-methyl-3-methylene-6-phenyl-hexyl)-6-cyclopropylcarbamoyloxy-4-hydroxy-7-(1-methoxy-1-methyl-ethoxy)-2,8-dioxa-bicyclo[3.2.1]octane-3,4,5-tricarboxylic acid tri-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:

2-tert-butyl-1,3-diisopropylisourea (71432-55-8) → (1S,3S,4S,5R,6R,7R)-1-((4S,5R)-4-Acetoxy-5-methyl-3-methylene-6-phenyl-hexyl)-6-cyclopropylcarbamoyloxy-4-hydroxy-7-(1-methoxy-1-methyl-ethoxy)-2,8-dioxa-bicyclo[3.2.1]octane-3,4,5-tricarboxylic acid tri-tert-butyl ester (146008-75-5)

Guidance literature:

Multi-step reaction with 5 steps

1: 86 percent / toluene / 16 h / 65 °C

2: 100 percent / pyridinium p-toluenesulfonate / CH₂Cl₂ / 2 h / Ambient temperature

3: 90 percent / hydroxylamine hydrochloride, sodium acetate trihydrate / methanol / 20 h / Ambient temperature

4: toluene / 6 h / Ambient temperature

5: toluene / 3 h / Ambient temperature

With hydroxylamine hydrochloride; sodium acetate; pyridinium p-toluenesulfonate; In methanol; dichloromethane; toluene;

DOI:10.1021/jm00049a022

Reference yield:

(1S,3S,4S,5R,6R,7R)-1-((4S,5R)-4-Acetoxy-5-methyl-3-methylene-6-phenyl-hexyl)-6-((E)-(4S,6S)-4,6-dimethyl-oct-2-enoyloxy)-4-hydroxy-7-(1-methoxy-1-methyl-ethoxy)-2,8-dioxa-bicyclo[3.2.1]octane-3,4,5-tricarboxylic acid tri-tert-butyl ester (146008-36-8) → (1S,3S,4S,5R,6R,7R)-1-((4S,5R)-4-Acetoxy-5-methyl-3-methylene-6-phenyl-hexyl)-6-cyclopropylcarbamoyloxy-4-hydroxy-7-(1-methoxy-1-methyl-ethoxy)-2,8-dioxa-bicyclo[3.2.1]octane-3,4,5-tricarboxylic acid tri-tert-butyl ester (146008-75-5)

Guidance literature:

Multi-step reaction with 3 steps

1: 90 percent / hydroxylamine hydrochloride, sodium acetate trihydrate / methanol / 20 h / Ambient temperature

2: toluene / 6 h / Ambient temperature

3: toluene / 3 h / Ambient temperature

With hydroxylamine hydrochloride; sodium acetate; In methanol; toluene;

DOI:10.1021/jm00049a022

Reference yield:

<1S-<1α(4R*,5R*),3α,4β,5α,6α(2E,4R*,6R*),7β>>-1-<4-(acetyloxy)-5-methyl-3-methylene-6-phenylhexyl>4,6,7-trihydroxy-2,8-dioxabicyclo<3.2.1>octane-3,4,5-tricarboxylic acid, 6-(4,6-dimethyl-2-octenoate), 3,4,5-tris(1,1-dimethylethyl) ester (144358-24-7) → (1S,3S,4S,5R,6R,7R)-1-((4S,5R)-4-Acetoxy-5-methyl-3-methylene-6-phenyl-hexyl)-6-cyclopropylcarbamoyloxy-4-hydroxy-7-(1-methoxy-1-methyl-ethoxy)-2,8-dioxa-bicyclo[3.2.1]octane-3,4,5-tricarboxylic acid tri-tert-butyl ester (146008-75-5)

Guidance literature:

Multi-step reaction with 4 steps

1: 100 percent / pyridinium p-toluenesulfonate / CH₂Cl₂ / 2 h / Ambient temperature

2: 90 percent / hydroxylamine hydrochloride, sodium acetate trihydrate / methanol / 20 h / Ambient temperature

3: toluene / 6 h / Ambient temperature

4: toluene / 3 h / Ambient temperature

With hydroxylamine hydrochloride; sodium acetate; pyridinium p-toluenesulfonate; In methanol; dichloromethane; toluene;

DOI:10.1021/jm00049a022

upstream raw materials:

(1S,3S,4S,5R,6R,7R)-1-((4S,5R)-4-Acetoxy-5-methyl-3-methylene-6-phenyl-hexyl)-4,6-dihydroxy-7-(1-methoxy-1-methyl-ethoxy)-2,8-dioxa-bicyclo[3.2.1]octane-3,4,5-tricarboxylic acid tri-tert-butyl ester

isocyanatocyclopropane

2-tert-butyl-1,3-diisopropylisourea

<1S-<1α(4R*,5R*),3α,4β,5α,6α(2E,4R*,6R*),7β>>-1-<4-(acetyloxy)-5-methyl-3-methylene-6-phenylhexyl>4,6,7-trihydroxy-2,8-dioxabicyclo<3.2.1>octane-3,4,5-tricarboxylic acid, 6-(4,6-dimethyl-2-octenoate), 3,4,5-tris(1,1-dimethylethyl) ester

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