(1S,3R,4R,6R,7S)-7-benzyloxy-1-benzyloxymethyl-3-(thymin-1-yl)-6-hydroxymethyl-2,5-dioxabicyclo[2.2.1]heptane

Base Information

• Chemical Name: (1S,3R,4R,6R,7S)-7-benzyloxy-1-benzyloxymethyl-3-(thymin-1-yl)-6-hydroxymethyl-2,5-dioxabicyclo[2.2.1]heptane
• CAS No.: 1052725-31-1
• Molecular Formula: C₂₆H₂₈N₂O₇
• Molecular Weight: 480.518

Synonyms:(1S,3R,4R,6R,7S)-7-benzyloxy-1-benzyloxymethyl-3-(thymin-1-yl)-6-hydroxymethyl-2,5-dioxabicyclo[2.2.1]heptane

Chemical Property of (1S,3R,4R,6R,7S)-7-benzyloxy-1-benzyloxymethyl-3-(thymin-1-yl)-6-hydroxymethyl-2,5-dioxabicyclo[2.2.1]heptane

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Technology Process of (1S,3R,4R,6R,7S)-7-benzyloxy-1-benzyloxymethyl-3-(thymin-1-yl)-6-hydroxymethyl-2,5-dioxabicyclo[2.2.1]heptane

There total 4 articles about (1S,3R,4R,6R,7S)-7-benzyloxy-1-benzyloxymethyl-3-(thymin-1-yl)-6-hydroxymethyl-2,5-dioxabicyclo[2.2.1]heptane 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: 83.0%

(1S,3R,4R,6R,7S)-7-benzyloxy-1-benzyloxymethyl-6-(2,2,6,6-tetramethylpiperidin-1-yl)oxymethyl-3-(thymin-1-yl)-2,5-dioxabicyclo[2.2.1]heptane (1052725-28-6) → (1S,3R,4R,6R,7S)-7-benzyloxy-1-benzyloxymethyl-3-(thymin-1-yl)-6-hydroxymethyl-2,5-dioxabicyclo[2.2.1]heptane (1052725-31-1)

Guidance literature:

With acetic acid; zinc; In tetrahydrofuran; water; at 65 ℃; for 1.5h;

DOI:10.1021/jo801081t

Reference yield: 55.0%

(1R,3R,4R,6S,7S)-7-benzyloxy-1-benzyloxymethyl-6-bromomercuriomethyl-3-(thymin-1-yl)-2,5-dioxabicyclo[2.2.1]heptane (1052725-23-1) → 1-(3,5-di-O-benzyl-4-C-vinyl-β-D-ribofuranosyl)thymine (1052725-26-4) + (1S,3R,4R,6R,7S)-7-benzyloxy-1-benzyloxymethyl-3-(thymin-1-yl)-6-hydroxymethyl-2,5-dioxabicyclo[2.2.1]heptane (1052725-31-1)

Guidance literature:

With sodium tetrahydroborate; oxygen; In N,N-dimethyl-formamide;

DOI:10.1021/jo801081t

Reference yield: 50.0%

1-(3,5-di-O-benzyl-4-C-(oxiran-1(S)-yl)-β-D-ribofuranosyl)thymine → (1S,3R,4R,6R,7S)-7-benzyloxy-1-benzyloxymethyl-3-(thymin-1-yl)-6-hydroxymethyl-2,5-dioxabicyclo[2.2.1]heptane (1052725-31-1)

Guidance literature:

With camphor-10-sulfonic acid; In dichloromethane; at 20 ℃; for 5h;

DOI:10.1021/jo801081t

upstream raw materials:

(1R,3R,4R,6S,7S)-7-benzyloxy-1-benzyloxymethyl-6-bromomercuriomethyl-3-(thymin-1-yl)-2,5-dioxabicyclo[2.2.1]heptane

(1S,3R,4R,6R,7S)-7-benzyloxy-1-benzyloxymethyl-6-(2,2,6,6-tetramethylpiperidin-1-yl)oxymethyl-3-(thymin-1-yl)-2,5-dioxabicyclo[2.2.1]heptane

1-(3,5-di-O-benzyl-4-C-vinyl-β-D-ribofuranosyl)thymine

Downstream raw materials:

(1S,3R,4R,6R,7S)-7-benzyloxy-1-benzyloxymethyl-6-methanesulfonyloxymethyl-3-(thymin-1-yl)-2,5-dioxabicyclo[2.2.1]heptane

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