(2R,3R,4R,5R)-5-((benzoyloxy)methyl)-3-ethynyl-3-hydroxytetrahydrofuran-2,4-diyl dibenzoate

Base Information

Chemical Name:(2R,3R,4R,5R)-5-((benzoyloxy)methyl)-3-ethynyl-3-hydroxytetrahydrofuran-2,4-diyl dibenzoate
CAS No.:1044589-96-9
Molecular Formula:C₂₈H₂₂O₈
Molecular Weight:486.478
Hs Code.:

Synonyms:(2R,3R,4R,5R)-5-((benzoyloxy)methyl)-3-ethynyl-3-hydroxytetrahydrofuran-2,4-diyl dibenzoate

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Chemical Property of (2R,3R,4R,5R)-5-((benzoyloxy)methyl)-3-ethynyl-3-hydroxytetrahydrofuran-2,4-diyl dibenzoate

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Technology Process of (2R,3R,4R,5R)-5-((benzoyloxy)methyl)-3-ethynyl-3-hydroxytetrahydrofuran-2,4-diyl dibenzoate

There total 3 articles about (2R,3R,4R,5R)-5-((benzoyloxy)methyl)-3-ethynyl-3-hydroxytetrahydrofuran-2,4-diyl dibenzoate 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:

: 22224-41-5
1,3,5-tri-O-benzoyl-α-D-ribofuranoside

: 1044589-96-9
(2R,3R,4R,5R)-5-((benzoyloxy)methyl)-3-ethynyl-3-hydroxytetrahydrofuran-2,4-diyl dibenzoate

Guidance literature:: Multi-step reaction with 2 steps

1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / acetonitrile / 16 h / 80 °C

2: tetrahydrofuran / 2 h / -78 - -30 °C

With 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione; In tetrahydrofuran; acetonitrile;

Reference yield:

: 157037-56-4
1,3,5-tri-O-benzoyl-2-oxo-α-D-erythro-pentofuranose

: 4301-14-8
acetylenemagnesium bromide

: 1044589-96-9
(2R,3R,4R,5R)-5-((benzoyloxy)methyl)-3-ethynyl-3-hydroxytetrahydrofuran-2,4-diyl dibenzoate

Guidance literature:: acetylenemagnesium bromide; With cerium(III) chloride; In tetrahydrofuran; at -50 - -30 ℃; for 1.83h;

(2R,4R,5R)-5-((benzoyloxy)methyl)-3-oxotetrahydrofuran-2,4-diyl dibenzoate; In tetrahydrofuran; at -50 - -30 ℃; for 3 - 4.16h;

With water; ammonium chloride; In tetrahydrofuran; at -50 - 20 ℃; Product distribution / selectivity;

Reference yield:

: 69339-86-2
1,2,3,5-tetra-O-benzoyl-α-D-ribofuranoside

: 1044589-96-9
(2R,3R,4R,5R)-5-((benzoyloxy)methyl)-3-ethynyl-3-hydroxytetrahydrofuran-2,4-diyl dibenzoate

Guidance literature:: Multi-step reaction with 2 steps

1: Dess-Martin periodane / dichloromethane

2: tetrahydrofuran / -70 - -40 °C

With Dess-Martin periodane; In tetrahydrofuran; dichloromethane; 1: |Dess-Martin Oxidation;
DOI:10.1016/j.bmcl.2018.04.069