(1S,2S,3R,4S,5S,6R)-3,5-Bis-benzyloxy-6-(4-methoxy-benzyloxy)-cyclohexane-1,2,4-triol

Base Information

• Chemical Name: (1S,2S,3R,4S,5S,6R)-3,5-Bis-benzyloxy-6-(4-methoxy-benzyloxy)-cyclohexane-1,2,4-triol
• CAS No.: 187980-87-6
• Molecular Formula: C₂₈H₃₂O₇
• Molecular Weight: 480.558

Synonyms:(1S,2S,3R,4S,5S,6R)-3,5-Bis-benzyloxy-6-(4-methoxy-benzyloxy)-cyclohexane-1,2,4-triol

Chemical Property of (1S,2S,3R,4S,5S,6R)-3,5-Bis-benzyloxy-6-(4-methoxy-benzyloxy)-cyclohexane-1,2,4-triol

Chemical Property:

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Technology Process of (1S,2S,3R,4S,5S,6R)-3,5-Bis-benzyloxy-6-(4-methoxy-benzyloxy)-cyclohexane-1,2,4-triol

There total 2 articles about (1S,2S,3R,4S,5S,6R)-3,5-Bis-benzyloxy-6-(4-methoxy-benzyloxy)-cyclohexane-1,2,4-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: 96.0%

(3aR,4S,5R,6S,7S,7aR)-4,6-Bis-benzyloxy-7-(4-methoxy-benzyloxy)-2,2-dimethyl-hexahydro-benzo[1,3]dioxol-5-ol (187979-42-6) → (1S,2S,3R,4S,5S,6R)-3,5-Bis-benzyloxy-6-(4-methoxy-benzyloxy)-cyclohexane-1,2,4-triol (187980-87-6)

Guidance literature:

With hydrogenchloride; acetone; In methanol; at 20 ℃; for 0.5h;

DOI:10.1016/S0008-6215(96)00211-X

Reference yield:

(1S,2R,4S)-4,7,7-Trimethyl-3-oxo-bicyclo[2.2.1]heptane-2-carboxylic acid (3aR,4R,5R,6R,7S,7aR)-4,6-bis-benzyloxy-7-(4-methoxy-benzyloxy)-2,2-dimethyl-hexahydro-benzo[1,3]dioxol-5-yl ester → (1S,2S,3R,4S,5S,6R)-3,5-Bis-benzyloxy-6-(4-methoxy-benzyloxy)-cyclohexane-1,2,4-triol (187980-87-6)

Guidance literature:

Multi-step reaction with 2 steps

2: 96 percent / HCl/acetone / methanol / 0.5 h / 20 °C

With hydrogenchloride; acetone; In methanol;

DOI:10.1016/S0008-6215(96)00211-X

Reference yield:

Dibenzyl N,N-diisopropylphosphoramidite (108549-23-1) + (1S,2S,3R,4S,5S,6R)-3,5-Bis-benzyloxy-6-(4-methoxy-benzyloxy)-cyclohexane-1,2,4-triol (187980-87-6) → Phosphorous acid dibenzyl ester (1R,2S,3R,4R,5S,6R)-2,6-bis-benzyloxy-3,4-bis-(bis-benzyloxy-phosphanyloxy)-5-(4-methoxy-benzyloxy)-cyclohexyl ester

Guidance literature:

With 1H-tetrazole; In dichloromethane; acetonitrile; at 20 ℃; for 1h;

DOI:10.1016/S0008-6215(96)00211-X

upstream raw materials:

(3aR,4S,5R,6S,7S,7aR)-4,6-Bis-benzyloxy-7-(4-methoxy-benzyloxy)-2,2-dimethyl-hexahydro-benzo[1,3]dioxol-5-ol

Downstream raw materials:

Phosphoric acid dibenzyl ester (1R,2S,3R,4R,5S,6R)-2,6-bis-benzyloxy-3,4-bis-(bis-benzyloxy-phosphoryloxy)-5-(4-methoxy-benzyloxy)-cyclohexyl ester

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