O-triisopropylsilyl 4-azido-4-deoxy-3,6-di-O-benzyl-[4-O-benzyl-2,3-di-O-isopropylidene-α-L-rhamnopyranose-(1->2)]-β-D-galactopyranoside

Base Information

Chemical Name:O-triisopropylsilyl 4-azido-4-deoxy-3,6-di-O-benzyl-[4-O-benzyl-2,3-di-O-isopropylidene-α-L-rhamnopyranose-(1->2)]-β-D-galactopyranoside
CAS No.:1392506-71-6
Molecular Formula:C₄₅H₆₃N₃O₉Si
Molecular Weight:818.095
Hs Code.:

Synonyms:O-triisopropylsilyl 4-azido-4-deoxy-3,6-di-O-benzyl-[4-O-benzyl-2,3-di-O-isopropylidene-α-L-rhamnopyranose-(1->2)]-β-D-galactopyranoside

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Chemical Property of O-triisopropylsilyl 4-azido-4-deoxy-3,6-di-O-benzyl-[4-O-benzyl-2,3-di-O-isopropylidene-α-L-rhamnopyranose-(1->2)]-β-D-galactopyranoside

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Technology Process of O-triisopropylsilyl 4-azido-4-deoxy-3,6-di-O-benzyl-[4-O-benzyl-2,3-di-O-isopropylidene-α-L-rhamnopyranose-(1->2)]-β-D-galactopyranoside

There total 1 articles about O-triisopropylsilyl 4-azido-4-deoxy-3,6-di-O-benzyl-[4-O-benzyl-2,3-di-O-isopropylidene-α-L-rhamnopyranose-(1->2)]-β-D-galactopyranoside 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: 82.0%

: 4-O-benzyl-2,3-di-O-isopropylidene-L-rhamnopyranoside

: 1189361-04-3
O-triisopropylsilyl 4-azido-4-deoxy-3,6-di-O-benzyl-β-D-galactopyranoside

: 1392506-71-6
O-triisopropylsilyl 4-azido-4-deoxy-3,6-di-O-benzyl-[4-O-benzyl-2,3-di-O-isopropylidene-α-L-rhamnopyranose-(1->2)]-β-D-galactopyranoside

Guidance literature:: 4-O-benzyl-2,3-di-O-isopropylidene-L-rhamnopyranoside; With 2,4,6-tri-tertbutylpyridine; trifluoromethylsulfonic anhydride; 1,1'-sulfinylbisbenzene; In dichloromethane; at -78 - -40 ℃; for 1.63333h; Inert atmosphere;

O-triisopropylsilyl 4-azido-4-deoxy-3,6-di-O-benzyl-β-D-galactopyranoside; In dichloromethane; at -78 - 21 ℃; for 11h; diastereoselective reaction; Inert atmosphere;
DOI:10.1021/ja305121q

Reference yield: 88.0%

: 1392506-71-6
O-triisopropylsilyl 4-azido-4-deoxy-3,6-di-O-benzyl-[4-O-benzyl-2,3-di-O-isopropylidene-α-L-rhamnopyranose-(1->2)]-β-D-galactopyranoside

: 4-azido-4-deoxy-3,6-di-O-benzyl-[4-O-benzyl-2,3-di-O-isopropylidene-α-L-rhamnopyranose-(1->3)]-D-galactopyranose

Guidance literature:: With tetrabutyl ammonium fluoride; acetic acid; In tetrahydrofuran; at 0 - 21 ℃; for 2.5h; Inert atmosphere;
DOI:10.1021/ja305121q

Reference yield:

: 1392506-71-6
O-triisopropylsilyl 4-azido-4-deoxy-3,6-di-O-benzyl-[4-O-benzyl-2,3-di-O-isopropylidene-α-L-rhamnopyranose-(1->2)]-β-D-galactopyranoside

: 1189361-42-9
O-trichloroacetimidoyl {[2,3,4-tri-O-benzyl-β-D-xylopyranosyl-(1->4)]-2,3-di-O-isopropylidene-L-rhamnopyranosyl-(1->2)}-4-azido-4-deoxy-3,6-di-O-benzyl-α-D-galactopyranoside

Guidance literature:: Multi-step reaction with 2 steps

1: tetrabutyl ammonium fluoride; acetic acid / tetrahydrofuran / 2.5 h / 0 - 21 °C / Inert atmosphere

2: 1,8-diazabicyclo[5.4.0]undec-7-ene / dichloromethane / 3.5 h / 0 °C / Inert atmosphere

With tetrabutyl ammonium fluoride; acetic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; In tetrahydrofuran; dichloromethane;
DOI:10.1021/ja305121q