O^β-(2,3,5-tri-O-benzyl-β-D-ribosyl)-N^α-benzyloxycarbonylserine benzyl ester

Base Information

Chemical Name:O^β-(2,3,5-tri-O-benzyl-β-D-ribosyl)-N^α-benzyloxycarbonylserine benzyl ester
CAS No.:1430197-90-2
Molecular Formula:C₄₄H₄₅NO₉
Molecular Weight:731.843
Hs Code.:

O<sup>β</sup>-(2,3,5-tri-O-benzyl-β-D-ribosyl)-N<sup>α</sup>-benzyloxycarbonylserine benzyl ester

Synonyms:O^β-(2,3,5-tri-O-benzyl-β-D-ribosyl)-N^α-benzyloxycarbonylserine benzyl ester

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Chemical Property of O^β-(2,3,5-tri-O-benzyl-β-D-ribosyl)-N^α-benzyloxycarbonylserine benzyl ester

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Technology Process of O^β-(2,3,5-tri-O-benzyl-β-D-ribosyl)-N^α-benzyloxycarbonylserine benzyl ester

There total 3 articles about O^β-(2,3,5-tri-O-benzyl-β-D-ribosyl)-N^α-benzyloxycarbonylserine benzyl ester 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: 58.0%

: 21209-51-8
N-benzyloxycarbonyl-L-serine benzyl ester

: C₂₈H₂₈Cl₃NO₅

: 1430197-69-5
O^β-(2,3,5-tri-O-benzyl-α-D-ribosyl)-N^α-benzyloxycarbonylserine benzyl ester

: 1430197-90-2
O^β-(2,3,5-tri-O-benzyl-β-D-ribosyl)-N^α-benzyloxycarbonylserine benzyl ester

Guidance literature:: With trimethylsilyl trifluoromethanesulfonate; In dichloromethane; at -20 ℃; for 0.5h; Molecular sieve; Inert atmosphere;
DOI:10.1021/jacs.1c05429

Reference yield:

: 21209-51-8
N-benzyloxycarbonyl-L-serine benzyl ester

: C₃₄H₃₂F₃NO₅

: 1430197-69-5
O^β-(2,3,5-tri-O-benzyl-α-D-ribosyl)-N^α-benzyloxycarbonylserine benzyl ester

: 1430197-90-2
O^β-(2,3,5-tri-O-benzyl-β-D-ribosyl)-N^α-benzyloxycarbonylserine benzyl ester

Guidance literature:: With trimethylsilyl trifluoromethanesulfonate; In dichloromethane; at -50 ℃; Overall yield = 78 %; Overall yield = 137 mg; stereoselective reaction; Molecular sieve; Inert atmosphere;
DOI:10.1021/ol400929c

Reference yield:

: 16838-89-4
2,3,5-tri-O-benzyl-D-ribofuranose

: 1430197-69-5
O^β-(2,3,5-tri-O-benzyl-α-D-ribosyl)-N^α-benzyloxycarbonylserine benzyl ester

: 1430197-90-2
O^β-(2,3,5-tri-O-benzyl-β-D-ribosyl)-N^α-benzyloxycarbonylserine benzyl ester

Guidance literature:: Multi-step reaction with 2 steps

1: potassium carbonate / dichloromethane / 20 °C

2: trimethylsilyl trifluoromethanesulfonate / dichloromethane / 0.5 h / -20 °C / Molecular sieve; Inert atmosphere

With trimethylsilyl trifluoromethanesulfonate; potassium carbonate; In dichloromethane;
DOI:10.1021/jacs.1c05429