(S)-N-((1S,2R,3R,4R,5R)-2-Benzyloxymethyl-3,4,5-trihydroxy-cyclopentyl)-2-hydroxy-2-phenyl-acetamide

Base Information

Chemical Name:(S)-N-((1S,2R,3R,4R,5R)-2-Benzyloxymethyl-3,4,5-trihydroxy-cyclopentyl)-2-hydroxy-2-phenyl-acetamide
CAS No.:207516-62-9
Molecular Formula:C₂₁H₂₅NO₆
Molecular Weight:387.433
Hs Code.:

Synonyms:(S)-N-((1S,2R,3R,4R,5R)-2-Benzyloxymethyl-3,4,5-trihydroxy-cyclopentyl)-2-hydroxy-2-phenyl-acetamide

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Chemical Property of (S)-N-((1S,2R,3R,4R,5R)-2-Benzyloxymethyl-3,4,5-trihydroxy-cyclopentyl)-2-hydroxy-2-phenyl-acetamide

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Technology Process of (S)-N-((1S,2R,3R,4R,5R)-2-Benzyloxymethyl-3,4,5-trihydroxy-cyclopentyl)-2-hydroxy-2-phenyl-acetamide

There total 3 articles about (S)-N-((1S,2R,3R,4R,5R)-2-Benzyloxymethyl-3,4,5-trihydroxy-cyclopentyl)-2-hydroxy-2-phenyl-acetamide 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: 52.0%

: 207516-56-1
(S)-N-((1S,2S,3R,4R,5R)-3-Benzyloxymethyl-4-hydroxy-6-oxa-bicyclo[3.1.0]hex-2-yl)-2-hydroxy-2-phenyl-acetamide

: 207516-61-8
(S)-N-((1S,2R,3R,4S,5S)-2-Benzyloxymethyl-3,4,5-trihydroxy-cyclopentyl)-2-hydroxy-2-phenyl-acetamide

: 207516-62-9
(S)-N-((1S,2R,3R,4R,5R)-2-Benzyloxymethyl-3,4,5-trihydroxy-cyclopentyl)-2-hydroxy-2-phenyl-acetamide

Guidance literature:: With trifluoroacetyl peroxide; In water; 1.) 0 deg C, 1 h, 2.) room temperature, 48 h;
DOI:10.1021/jo980050a

Reference yield:

: 39939-07-6
5-(benzyloxymethyl)cyclopentadiene

: 207516-62-9
(S)-N-((1S,2R,3R,4R,5R)-2-Benzyloxymethyl-3,4,5-trihydroxy-cyclopentyl)-2-hydroxy-2-phenyl-acetamide

Guidance literature:: Multi-step reaction with 3 steps

1: 1.) n-Bu₄NIO₄, 2.) Na/Hg / 1.) MeOH, -20 deg C, 24 h, 2.) THF, MeOH, 0 deg C, 8 h

2: 96 percent / m-CPBA / dioxane / Ambient temperature

3: 52 percent / CF₃CO₃H / H₂O / 1.) 0 deg C, 1 h, 2.) room temperature, 48 h

With sodium amalgam; trifluoroacetyl peroxide; tetrabutylammonium periodite; 3-chloro-benzenecarboperoxoic acid; In 1,4-dioxane; water;
DOI:10.1021/jo980050a

Reference yield:

: 207516-06-1
(S)-N-((1R,4S,5R)-5-Benzyloxymethyl-4-hydroxy-cyclopent-2-enyl)-2-hydroxy-2-phenyl-acetamide

: 207516-62-9
(S)-N-((1S,2R,3R,4R,5R)-2-Benzyloxymethyl-3,4,5-trihydroxy-cyclopentyl)-2-hydroxy-2-phenyl-acetamide

Guidance literature:: Multi-step reaction with 2 steps

1: 96 percent / m-CPBA / dioxane / Ambient temperature

2: 52 percent / CF₃CO₃H / H₂O / 1.) 0 deg C, 1 h, 2.) room temperature, 48 h

With trifluoroacetyl peroxide; 3-chloro-benzenecarboperoxoic acid; In 1,4-dioxane; water;
DOI:10.1021/jo980050a