(2S)-2-[(N-benzyloxycarbonyl-D-alaninyl)amino]propyl 2-O-acetyl-3,4-di-O-methyl-α-L-rhamnopyranoside

Base Information

Chemical Name:(2S)-2-[(N-benzyloxycarbonyl-D-alaninyl)amino]propyl 2-O-acetyl-3,4-di-O-methyl-α-L-rhamnopyranoside
CAS No.:138588-03-1
Molecular Formula:C₂₄H₃₆N₂O₉
Molecular Weight:496.558
Hs Code.:

Synonyms:(2S)-2-[(N-benzyloxycarbonyl-D-alaninyl)amino]propyl 2-O-acetyl-3,4-di-O-methyl-α-L-rhamnopyranoside

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Chemical Property of (2S)-2-[(N-benzyloxycarbonyl-D-alaninyl)amino]propyl 2-O-acetyl-3,4-di-O-methyl-α-L-rhamnopyranoside

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Technology Process of (2S)-2-[(N-benzyloxycarbonyl-D-alaninyl)amino]propyl 2-O-acetyl-3,4-di-O-methyl-α-L-rhamnopyranoside

There total 15 articles about (2S)-2-[(N-benzyloxycarbonyl-D-alaninyl)amino]propyl 2-O-acetyl-3,4-di-O-methyl-α-L-rhamnopyranoside 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: 81.0%

: 683772-92-1
N-benzyloxycarbonyl-D-alaninyl-L-alaninol

: 683773-35-5
1,2-O-[(S)-1-(4-pentenyloxy)ethylidene]-3,4-di-O-methyl-β-L-rhamnopyranose

: 138588-03-1
(2S)-2-[(N-benzyloxycarbonyl-D-alaninyl)amino]propyl 2-O-acetyl-3,4-di-O-methyl-α-L-rhamnopyranoside

Guidance literature:: With N-iodo-succinimide; trimethylsilyl trifluoromethanesulfonate; In dichloromethane; at 20 ℃; for 0.5h;
DOI:10.1021/jo030304e

Reference yield: 72.0%

: 142739-21-7
2-O-acetyl-3,4-di-O-methyl-α-L-rhamnopyranosyl trichloroacetimidate

: 683772-92-1
N-benzyloxycarbonyl-D-alaninyl-L-alaninol

: 138588-03-1
(2S)-2-[(N-benzyloxycarbonyl-D-alaninyl)amino]propyl 2-O-acetyl-3,4-di-O-methyl-α-L-rhamnopyranoside

Guidance literature:: With trimethylsilyl trifluoromethanesulfonate; 4 A molecular sieve; In dichloromethane; cooling;
DOI:10.1021/jo030304e

Reference yield:

: 5158-64-5
2,3,4-tri-O-acetyl-α-L-rhamnopyranosyl bromide

: 138588-03-1
(2S)-2-[(N-benzyloxycarbonyl-D-alaninyl)amino]propyl 2-O-acetyl-3,4-di-O-methyl-α-L-rhamnopyranoside

Guidance literature:: Multi-step reaction with 3 steps

1.1: 87 percent / 2,6-lutidine / CHCl₃ / 48 h / 20 °C

2.1: NaOH / dioxane / 2 h / 20 °C

2.2: 92 percent / dioxane

3.1: 81 percent / NIS; TMS triflate / CH₂Cl₂ / 0.5 h / 20 °C

With 2,6-dimethylpyridine; sodium hydroxide; N-iodo-succinimide; trimethylsilyl trifluoromethanesulfonate; In 1,4-dioxane; dichloromethane; chloroform;
DOI:10.1021/jo030304e