(1R,2R,5S,7R,8S)-8-benzyloxy-5-benzyloxymethyl-2-methyl-4-oxo-7-(thymin-1-yl)-6-oxabicyclo[3.2.1]octane

Base Information

• Chemical Name: (1R,2R,5S,7R,8S)-8-benzyloxy-5-benzyloxymethyl-2-methyl-4-oxo-7-(thymin-1-yl)-6-oxabicyclo[3.2.1]octane
• CAS No.: 1095154-39-4
• Molecular Formula: C₂₈H₃₀N₂O₆
• Molecular Weight: 490.556

Synonyms:(1R,2R,5S,7R,8S)-8-benzyloxy-5-benzyloxymethyl-2-methyl-4-oxo-7-(thymin-1-yl)-6-oxabicyclo[3.2.1]octane

Chemical Property of (1R,2R,5S,7R,8S)-8-benzyloxy-5-benzyloxymethyl-2-methyl-4-oxo-7-(thymin-1-yl)-6-oxabicyclo[3.2.1]octane

Chemical Property:

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Technology Process of (1R,2R,5S,7R,8S)-8-benzyloxy-5-benzyloxymethyl-2-methyl-4-oxo-7-(thymin-1-yl)-6-oxabicyclo[3.2.1]octane

There total 1 articles about (1R,2R,5S,7R,8S)-8-benzyloxy-5-benzyloxymethyl-2-methyl-4-oxo-7-(thymin-1-yl)-6-oxabicyclo[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: 90.0%

(1R,2R,4S,5S,7R,8S)-8-benzyloxy-5-benzyloxymethyl-4-hydroxy-2-methyl-7-(thymin-1-yl)-6-oxabicyclo[3.2.1]octane (1095154-37-2) → (1R,2R,5S,7R,8S)-8-benzyloxy-5-benzyloxymethyl-2-methyl-4-oxo-7-(thymin-1-yl)-6-oxabicyclo[3.2.1]octane (1095154-39-4)

Guidance literature:

With Dess-Martin periodane; In dichloromethane; at 20 ℃; for 1.5h; Inert atmosphere;

DOI:10.1021/jo8016742

Reference yield: 90.0%

methyl magnesium iodide (917-64-6) + (1R,2R,5S,7R,8S)-8-benzyloxy-5-benzyloxymethyl-2-methyl-4-oxo-7-(thymin-1-yl)-6-oxabicyclo[3.2.1]octane (1095154-39-4) → (1R,2R,4R,5R,7R,8S)-8-benzyloxy-5-benzyloxymethyl-2,4-dimethyl-4-hydroxy-7-(thymin-1-yl)-6-oxabicyclo[3.2.1]octane (1095154-43-0)

Guidance literature:

methyl magnesium iodide; (1R,2R,5S,7R,8S)-8-benzyloxy-5-benzyloxymethyl-2-methyl-4-oxo-7-(thymin-1-yl)-6-oxabicyclo[3.2.1]octane; In tetrahydrofuran; diethyl ether; at 0 - 20 ℃; Inert atmosphere;

With ammonium chloride; In tetrahydrofuran; diethyl ether;

DOI:10.1021/jo8016742

Reference yield: 82.0%

(1R,2R,5S,7R,8S)-8-benzyloxy-5-benzyloxymethyl-2-methyl-4-oxo-7-(thymin-1-yl)-6-oxabicyclo[3.2.1]octane (1095154-39-4) → (1R,2R,4R,5S,7R,8S)-8-benzyloxy-5-benzyloxymethyl-4-hydroxy-2-methyl-7-(thymin-1-yl)-6-oxabicyclo[3.2.1]octane (1095154-41-8)

Guidance literature:

With sodium tetrahydroborate; In ethanol; at 20 ℃;

DOI:10.1021/jo8016742

upstream raw materials:

(1R,2R,4S,5S,7R,8S)-8-benzyloxy-5-benzyloxymethyl-4-hydroxy-2-methyl-7-(thymin-1-yl)-6-oxabicyclo[3.2.1]octane

Downstream raw materials:

(1R,2R,4R,5S,7R,8S)-8-benzyloxy-5-benzyloxymethyl-4-hydroxy-2-methyl-7-(thymin-1-yl)-6-oxabicyclo[3.2.1]octane

(1R,2R,4R,5R,7R,8S)-8-benzyloxy-5-benzyloxymethyl-2,4-dimethyl-4-hydroxy-7-(thymin-1-yl)-6-oxabicyclo[3.2.1]octane

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