(1R,5R,7R,8S)-8-benzyloxy-5-benzyloxymethyl-4-one-7-(thymin-1-yl)-6-oxa-bicyclo[3.2.1]octane

Base Information

• Chemical Name: (1R,5R,7R,8S)-8-benzyloxy-5-benzyloxymethyl-4-one-7-(thymin-1-yl)-6-oxa-bicyclo[3.2.1]octane
• CAS No.: 1104192-38-2
• Molecular Formula: C₂₇H₂₈N₂O₆
• Molecular Weight: 476.529

Synonyms:(1R,5R,7R,8S)-8-benzyloxy-5-benzyloxymethyl-4-one-7-(thymin-1-yl)-6-oxa-bicyclo[3.2.1]octane

Chemical Property of (1R,5R,7R,8S)-8-benzyloxy-5-benzyloxymethyl-4-one-7-(thymin-1-yl)-6-oxa-bicyclo[3.2.1]octane

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Technology Process of (1R,5R,7R,8S)-8-benzyloxy-5-benzyloxymethyl-4-one-7-(thymin-1-yl)-6-oxa-bicyclo[3.2.1]octane

There total 1 articles about (1R,5R,7R,8S)-8-benzyloxy-5-benzyloxymethyl-4-one-7-(thymin-1-yl)-6-oxa-bicyclo[3.2.1]octane 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:

1-[3,5-di-O-benzyl-4-C-(1-hydroxy-allyl)-2-O-phenoxythiocarbonyl-β-D-ribofuranosyl]thymine (1095153-47-1) → (1R,3R,4R,5R,7S)-7-benzyloxy-1-benzyloxymethyl-5-methyl-6-oxo-3-(thymin-1-yl)-2-oxa-bicyclo[2.2.1]heptane (1095153-53-9) + (1R,5R,7R,8S)-8-benzyloxy-5-benzyloxymethyl-4-one-7-(thymin-1-yl)-6-oxa-bicyclo[3.2.1]octane (1104192-38-2)

Guidance literature:

1-[3,5-di-O-benzyl-4-C-(1-hydroxy-allyl)-2-O-phenoxythiocarbonyl-β-D-ribofuranosyl]thymine; With 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride; In toluene; for 4h; Reflux;

With Dess-Martin periodane; In dichloromethane; at 20 ℃; for 2h;

DOI:10.1039/b813870b

Reference yield: 81.0%

(1R,5R,7R,8S)-8-benzyloxy-5-benzyloxymethyl-4-one-7-(thymin-1-yl)-6-oxa-bicyclo[3.2.1]octane (1104192-38-2) → (1R,4R,5S,7R,8S)-8-benzyloxy-5-benzyloxymethyl-4-hydroxy-7-(thymin-1-yl)-6-oxa-bicyclo[3.2.1]octane (1104192-39-3)

Guidance literature:

With sodium tetrahydroborate; In ethanol; water; at 20 ℃; stereoselective reaction;

DOI:10.1039/b813870b

upstream raw materials:

1-[3,5-di-O-benzyl-4-C-(1-hydroxy-allyl)-2-O-phenoxythiocarbonyl-β-D-ribofuranosyl]thymine

Downstream raw materials:

(1R,4R,5S,7R,8S)-8-benzyloxy-5-benzyloxymethyl-4-hydroxy-7-(thymin-1-yl)-6-oxa-bicyclo[3.2.1]octane

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