Carbonic acid (3aR,4S,5R,5aR,8aS,8bR)-5-benzyloxy-2,2,7,7-tetramethyl-hexahydro-benzo[1,2-d;3,4-d']bis[1,3]dioxol-4-yl ester (1S,2R,5S)-2-isopropyl-5-methyl-cyclohexyl ester

Base Information

• Chemical Name: Carbonic acid (3aR,4S,5R,5aR,8aS,8bR)-5-benzyloxy-2,2,7,7-tetramethyl-hexahydro-benzo[1,2-d;3,4-d']bis[1,3]dioxol-4-yl ester (1S,2R,5S)-2-isopropyl-5-methyl-cyclohexyl ester
• CAS No.: 207131-20-2
• Molecular Formula: C₃₀H₄₄O₈
• Molecular Weight: 532.675
• Mol file: 207131-20-2.mol

Synonyms:

Chemical Property of Carbonic acid (3aR,4S,5R,5aR,8aS,8bR)-5-benzyloxy-2,2,7,7-tetramethyl-hexahydro-benzo[1,2-d;3,4-d']bis[1,3]dioxol-4-yl ester (1S,2R,5S)-2-isopropyl-5-methyl-cyclohexyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Carbonic acid (3aR,4S,5R,5aR,8aS,8bR)-5-benzyloxy-2,2,7,7-tetramethyl-hexahydro-benzo[1,2-d;3,4-d']bis[1,3]dioxol-4-yl ester (1S,2R,5S)-2-isopropyl-5-methyl-cyclohexyl ester

There total 1 articles about Carbonic acid (3aR,4S,5R,5aR,8aS,8bR)-5-benzyloxy-2,2,7,7-tetramethyl-hexahydro-benzo[1,2-d;3,4-d']bis[1,3]dioxol-4-yl ester (1S,2R,5S)-2-isopropyl-5-methyl-cyclohexyl 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: 28.0%

(+)-(1S,2R,5S)-menthylchloroformate (7635-54-3,7635-53-2) + (3aR,4R,5R,5aS,8aR,8bR)-5-Benzyloxy-2,2,7,7-tetramethyl-hexahydro-benzo[1,2-d;3,4-d']bis[1,3]dioxol-4-ol → Carbonic acid (3aR,4S,5R,5aR,8aS,8bR)-5-benzyloxy-2,2,7,7-tetramethyl-hexahydro-benzo[1,2-d;3,4-d']bis[1,3]dioxol-4-yl ester (1S,2R,5S)-2-isopropyl-5-methyl-cyclohexyl ester (207131-20-2) + Carbonic acid (3aS,4R,5S,5aS,8aR,8bS)-5-benzyloxy-2,2,7,7-tetramethyl-hexahydro-benzo[1,2-d;3,4-d']bis[1,3]dioxol-4-yl ester (1S,2R,5S)-2-isopropyl-5-methyl-cyclohexyl ester

Guidance literature:

With pyridine; In dichloromethane; Ambient temperature;

DOI:10.1016/S0008-6215(97)00267-X

Reference yield:

Carbonic acid (3aR,4S,5R,5aR,8aS,8bR)-5-benzyloxy-2,2,7,7-tetramethyl-hexahydro-benzo[1,2-d;3,4-d']bis[1,3]dioxol-4-yl ester (1S,2R,5S)-2-isopropyl-5-methyl-cyclohexyl ester (207131-20-2) → D-myo-inositol 1,4,5-triphosphate (2068-89-5,28841-61-4,72002-56-3,85166-31-0,88269-39-0,91840-07-2,91840-10-7,92216-45-0,93133-75-6,93133-76-7,98102-63-7,109583-09-7,112294-76-5,114418-80-3,114418-81-4,114418-82-5,114418-84-7,114418-85-8,115184-70-8,121251-06-7,121251-11-4,122742-32-9,125135-23-1,129706-79-2,131321-72-7,131321-73-8,131321-75-0,136521-83-0,136597-98-3,136597-99-4,136735-76-7,145163-95-7)

Guidance literature:

Multi-step reaction with 3 steps

1: 1.) pyridinium p-toluenesulfonate, 2.) potassium carbonate / 1.) CH₂Cl₂, ethylene glycol, reflux, 10 h, 2.) methanol, reflux, 1 h

2: 1.) 1H-tetrazole, 2.) m-chloroperoxybenzoic acid / 1.) CH₂Cl₂, room temperature, 30 min, 2.) CH₂Cl₂, -40 deg C -> room temperature

3: glacial acetic acid, hydrogen / palladium/charcoal / ethanol; H₂O

With 1H-tetrazole; hydrogen; pyridinium p-toluenesulfonate; potassium carbonate; acetic acid; 3-chloro-benzenecarboperoxoic acid; palladium on activated charcoal; In ethanol; water;

DOI:10.1016/S0008-6215(97)00267-X

Reference yield:

Carbonic acid (3aR,4S,5R,5aR,8aS,8bR)-5-benzyloxy-2,2,7,7-tetramethyl-hexahydro-benzo[1,2-d;3,4-d']bis[1,3]dioxol-4-yl ester (1S,2R,5S)-2-isopropyl-5-methyl-cyclohexyl ester (207131-20-2) → Carbonic acid (3aR,4S,5R,6S,7S,7aR)-5-benzyloxy-6,7-dihydroxy-2,2-dimethyl-hexahydro-benzo[1,3]dioxol-4-yl ester (1S,2R,5S)-2-isopropyl-5-methyl-cyclohexyl ester

Guidance literature:

With pyridinium p-toluenesulfonate; In dichloromethane; ethylene glycol; for 10h; Heating;

DOI:10.1016/S0008-6215(97)00267-X

upstream raw materials:

(+)-(1S,2R,5S)-menthylchloroformate

Downstream raw materials:

(3aR,4S,5S,6R,7S,7aS)-6-Benzyloxy-2,2-dimethyl-hexahydro-benzo[1,3]dioxole-4,5,7-triol

D-myo-inositol 1,4,5-triphosphate

4-O-benzyl-1,2-O-isopropylidene-myoinositol 3,5,6-tris(dibenzyl phosphate)