(3aR,5R,6R,7S,7aS)-6,7-Bis-benzyloxy-5-benzyloxymethyl-hexahydro-furo[3,2-b]pyran-2-ol

Base Information

• Chemical Name: (3aR,5R,6R,7S,7aS)-6,7-Bis-benzyloxy-5-benzyloxymethyl-hexahydro-furo[3,2-b]pyran-2-ol
• CAS No.: 190511-65-0
• Molecular Formula: C₂₉H₃₂O₆
• Molecular Weight: 476.569

Synonyms:(3aR,5R,6R,7S,7aS)-6,7-Bis-benzyloxy-5-benzyloxymethyl-hexahydro-furo[3,2-b]pyran-2-ol

Chemical Property of (3aR,5R,6R,7S,7aS)-6,7-Bis-benzyloxy-5-benzyloxymethyl-hexahydro-furo[3,2-b]pyran-2-ol

Chemical Property:

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Technology Process of (3aR,5R,6R,7S,7aS)-6,7-Bis-benzyloxy-5-benzyloxymethyl-hexahydro-furo[3,2-b]pyran-2-ol

There total 2 articles about (3aR,5R,6R,7S,7aS)-6,7-Bis-benzyloxy-5-benzyloxymethyl-hexahydro-furo[3,2-b]pyran-2-ol 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%

(3aR,5R,6R,7S,7aS)-6,7-Bis-benzyloxy-5-benzyloxymethyl-hexahydro-furo[3,2-b]pyran-2-one (190511-64-9) → (3aR,5R,6R,7S,7aS)-6,7-Bis-benzyloxy-5-benzyloxymethyl-hexahydro-furo[3,2-b]pyran-2-ol (190511-65-0)

Guidance literature:

With diisobutylaluminium hydride; In dichloromethane; at -78 ℃;

DOI:10.1016/S0040-4039(97)00576-5

Reference yield:

(5R,6R,7S)-6,7-Bis-benzyloxy-5-benzyloxymethyl-3,3-dichloro-hexahydro-furo[3,2-b]pyran-2-one (190511-63-8) → (3aR,5R,6R,7S,7aS)-6,7-Bis-benzyloxy-5-benzyloxymethyl-hexahydro-furo[3,2-b]pyran-2-ol (190511-65-0)

Guidance literature:

Multi-step reaction with 2 steps

1: Zn / acetic acid / 80 °C

2: 85 percent / diisobutylaluminum hydride / CH₂Cl₂ / -78 °C

With diisobutylaluminium hydride; zinc; In dichloromethane; acetic acid;

DOI:10.1016/S0040-4039(97)00576-5

Reference yield: 90.0%

(3aR,5R,6R,7S,7aS)-6,7-Bis-benzyloxy-5-benzyloxymethyl-hexahydro-furo[3,2-b]pyran-2-ol (190511-65-0) → Formic acid (2S,3R,4S,5R,6R)-4,5-bis-benzyloxy-6-benzyloxymethyl-2-iodomethyl-tetrahydro-pyran-3-yl ester (190511-66-1)

Guidance literature:

With [bis(acetoxy)iodo]benzene; iodine; In cyclohexane; benzene; Irradiation;

DOI:10.1016/S0040-4039(97)00576-5

upstream raw materials:

(3aR,5R,6R,7S,7aS)-6,7-Bis-benzyloxy-5-benzyloxymethyl-hexahydro-furo[3,2-b]pyran-2-one

(5R,6R,7S)-6,7-Bis-benzyloxy-5-benzyloxymethyl-3,3-dichloro-hexahydro-furo[3,2-b]pyran-2-one

Downstream raw materials:

Formic acid (2S,3R,4S,5R,6R)-4,5-bis-benzyloxy-6-benzyloxymethyl-2-iodomethyl-tetrahydro-pyran-3-yl ester

Acetic acid (3aR,5R,6R,7S,7aS)-6,7-bis-benzyloxy-5-benzyloxymethyl-hexahydro-furo[3,2-b]pyran-2-yl ester

1-((2R,3aR,5R,6R,7S,7aS)-6,7-Bis-benzyloxy-5-benzyloxymethyl-hexahydro-furo[3,2-b]pyran-2-yl)-1H-pyrimidine-2,4-dione

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