(E/Z)-2-buten-2-yl 3,4,6-tri-O-benzyl-2-azido-2-deoxy-β-D-glucopyranoside

Base Information

Chemical Name:(E/Z)-2-buten-2-yl 3,4,6-tri-O-benzyl-2-azido-2-deoxy-β-D-glucopyranoside
CAS No.:312612-87-6
Molecular Formula:C₃₁H₃₅N₃O₅
Molecular Weight:529.636
Hs Code.:

Synonyms:(E/Z)-2-buten-2-yl 3,4,6-tri-O-benzyl-2-azido-2-deoxy-β-D-glucopyranoside

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Chemical Property of (E/Z)-2-buten-2-yl 3,4,6-tri-O-benzyl-2-azido-2-deoxy-β-D-glucopyranoside

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Technology Process of (E/Z)-2-buten-2-yl 3,4,6-tri-O-benzyl-2-azido-2-deoxy-β-D-glucopyranoside

There total 4 articles about (E/Z)-2-buten-2-yl 3,4,6-tri-O-benzyl-2-azido-2-deoxy-β-D-glucopyranoside 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%

: 312612-86-5
(R/S)-3-buten-2-yl 3,4,6-tri-O-benzyl-2-azido-2-deoxy-β-D-glucopyranoside

: 312612-87-6
(E/Z)-2-buten-2-yl 3,4,6-tri-O-benzyl-2-azido-2-deoxy-β-D-glucopyranoside

Guidance literature:: With Wilkinson's catalyst; n-butyllithium; In tetrahydrofuran; for 2h; Heating;
DOI:10.1080/07328300008544127

Reference yield:

: 312612-84-3
(R/S)-3-buten-2-yl 2-amino-2-deoxy-β-D-glucopyranoside

: 312612-87-6
(E/Z)-2-buten-2-yl 3,4,6-tri-O-benzyl-2-azido-2-deoxy-β-D-glucopyranoside

Guidance literature:: Multi-step reaction with 3 steps

1: TfN₃; DMAP; CuSO₄ hydrate / methanol / 36 h

2: 0.92 g / NaH / dimethylformamide / 2 h / 20 °C

3: 90 percent / (Ph₃P)3RhCl; n-BuLi / tetrahydrofuran / 2 h / Heating

With dmap; Wilkinson's catalyst; n-butyllithium; triflic azide; sodium hydride; copper(II) sulfate; In tetrahydrofuran; methanol; N,N-dimethyl-formamide; 1: Substitution / 2: Alkylation / 3: Isomerization;
DOI:10.1080/07328300008544127

Reference yield:

: (2R,3S,4R,5R,6R)-5-Azido-2-hydroxymethyl-6-(1-methyl-allyloxy)-tetrahydro-pyran-3,4-diol

: 312612-87-6
(E/Z)-2-buten-2-yl 3,4,6-tri-O-benzyl-2-azido-2-deoxy-β-D-glucopyranoside

Guidance literature:: Multi-step reaction with 2 steps

1: 0.92 g / NaH / dimethylformamide / 2 h / 20 °C

2: 90 percent / (Ph₃P)3RhCl; n-BuLi / tetrahydrofuran / 2 h / Heating

With Wilkinson's catalyst; n-butyllithium; sodium hydride; In tetrahydrofuran; N,N-dimethyl-formamide; 1: Alkylation / 2: Isomerization;
DOI:10.1080/07328300008544127