4-azido-3-O-benzyl-4,6-dideoxy-2-O-methyl-β-D-glucopyranosyl-(1->3)-2-O-acetyl-4-O-benzyl-α-L-rhamnopyranosyl trichloroacetimidate

Base Information

Chemical Name:4-azido-3-O-benzyl-4,6-dideoxy-2-O-methyl-β-D-glucopyranosyl-(1->3)-2-O-acetyl-4-O-benzyl-α-L-rhamnopyranosyl trichloroacetimidate
CAS No.:870543-42-3
Molecular Formula:C₃₁H₃₇Cl₃N₄O₉
Molecular Weight:716.015
Hs Code.:

Synonyms:4-azido-3-O-benzyl-4,6-dideoxy-2-O-methyl-β-D-glucopyranosyl-(1->3)-2-O-acetyl-4-O-benzyl-α-L-rhamnopyranosyl trichloroacetimidate

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Chemical Property of 4-azido-3-O-benzyl-4,6-dideoxy-2-O-methyl-β-D-glucopyranosyl-(1->3)-2-O-acetyl-4-O-benzyl-α-L-rhamnopyranosyl trichloroacetimidate

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Technology Process of 4-azido-3-O-benzyl-4,6-dideoxy-2-O-methyl-β-D-glucopyranosyl-(1->3)-2-O-acetyl-4-O-benzyl-α-L-rhamnopyranosyl trichloroacetimidate

There total 6 articles about 4-azido-3-O-benzyl-4,6-dideoxy-2-O-methyl-β-D-glucopyranosyl-(1->3)-2-O-acetyl-4-O-benzyl-α-L-rhamnopyranosyl trichloroacetimidate 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:

: C₂₉H₃₇N₃O₉

: 545-06-2
trichloroacetonitrile

: 870543-42-3
4-azido-3-O-benzyl-4,6-dideoxy-2-O-methyl-β-D-glucopyranosyl-(1->3)-2-O-acetyl-4-O-benzyl-α-L-rhamnopyranosyl trichloroacetimidate

Guidance literature:: sodium hydride; In dichloromethane; at 25 ℃; for 1h;

Reference yield:

: Acetic acid (3R,4R,5S,6S)-4-((2S,3R,4S,5R,6R)-5-azido-4-benzyloxy-3-methoxy-6-methyl-tetrahydro-pyran-2-yloxy)-5-benzyloxy-2-hydroxy-6-methyl-tetrahydro-pyran-3-yl ester

: 545-06-2
trichloroacetonitrile

: 870543-42-3
4-azido-3-O-benzyl-4,6-dideoxy-2-O-methyl-β-D-glucopyranosyl-(1->3)-2-O-acetyl-4-O-benzyl-α-L-rhamnopyranosyl trichloroacetimidate

Guidance literature:: With sodium hydride; In dichloromethane; at 25 ℃; for 1h;
DOI:10.1002/anie.200502615

Reference yield:

: 870543-37-6
p-methoxyphenyl 2-O-acetyl-4-O-benzyl-α-L-rhamnopyranoside

: 870543-42-3
4-azido-3-O-benzyl-4,6-dideoxy-2-O-methyl-β-D-glucopyranosyl-(1->3)-2-O-acetyl-4-O-benzyl-α-L-rhamnopyranosyl trichloroacetimidate

Guidance literature:: Multi-step reaction with 5 steps

1: 90 percent / trimethylsilyl trifluoromethanesulfonate / CH₂Cl₂ / 1 h / 0 °C

2: 100 percent / hydrazinium acetate / CH₂Cl₂; methanol / 12 h / 25 °C

3: 73 percent / silver(I) oxide; dimethyl sulfide / tetrahydrofuran / 8 h / 25 °C

4: cerium(IV) ammonium nitrate / acetonitrile; H₂O / 1.5 h / 25 °C

5: 125 mg / sodium hydride / CH₂Cl₂ / 1 h / 25 °C

With ammonium cerium(IV) nitrate; dimethylsulfide; trimethylsilyl trifluoromethanesulfonate; hydrazinium monoacetate; sodium hydride; silver(l) oxide; In tetrahydrofuran; methanol; dichloromethane; water; acetonitrile;
DOI:10.1002/anie.200502615