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

Base Information

• Chemical Name: (3aR,4S,5S,6R,7S,7aS)-6-Benzyloxy-2,2-dimethyl-hexahydro-benzo[1,3]dioxole-4,5,7-triol
• CAS No.: 139640-12-3
• Molecular Formula: C₁₆H₂₂O₆
• Molecular Weight: 310.347

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

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

Chemical Property:

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

There total 4 articles about (3aR,4S,5S,6R,7S,7aS)-6-Benzyloxy-2,2-dimethyl-hexahydro-benzo[1,3]dioxole-4,5,7-triol 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: 85.0%

(3aS,4S,5S,5aR,8aS,8bS)-5-Benzyloxy-2,2,7,7-tetramethyl-hexahydro-benzo[1,2-d;3,4-d']bis[1,3]dioxol-4-ol (139686-87-6) → (3aR,4S,5S,6R,7S,7aS)-6-Benzyloxy-2,2-dimethyl-hexahydro-benzo[1,3]dioxole-4,5,7-triol (139640-12-3)

Guidance literature:

With pyridinium p-toluenesulfonate;

DOI:10.1016/S0040-4039(00)74142-6

Reference yield:

1-O-menthoxycarbonyl-2,3:4,5-di-O-isopropylidene-myo-inositol (139640-09-8) → (3aR,4S,5S,6R,7S,7aS)-6-Benzyloxy-2,2-dimethyl-hexahydro-benzo[1,3]dioxole-4,5,7-triol (139640-12-3)

Guidance literature:

Multi-step reaction with 3 steps

1: 91 percent / Ag₂O

2: 90 percent / NaOMe / methanol

3: 85 percent / pyridinium p-toluenesulphonate

With sodium methylate; pyridinium p-toluenesulfonate; silver(l) oxide; In methanol;

DOI:10.1016/S0040-4039(00)74142-6

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 (1R,2S,5R)-2-isopropyl-5-methyl-cyclohexyl ester (139640-11-2) → (3aR,4S,5S,6R,7S,7aS)-6-Benzyloxy-2,2-dimethyl-hexahydro-benzo[1,3]dioxole-4,5,7-triol (139640-12-3)

Guidance literature:

Multi-step reaction with 2 steps

1: 90 percent / NaOMe / methanol

2: 85 percent / pyridinium p-toluenesulphonate

With sodium methylate; pyridinium p-toluenesulfonate; In methanol;

DOI:10.1016/S0040-4039(00)74142-6

upstream raw materials:

(3aS,4S,5S,5aR,8aS,8bS)-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

1-O-menthoxycarbonyl-2,3:4,5-di-O-isopropylidene-myo-inositol

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 (1R,2S,5R)-2-isopropyl-5-methyl-cyclohexyl ester

Downstream raw materials:

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

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

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