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

Base Information

Chemical Name:4-methoxyphenyl 4-azido-3-O-benzyl-4,6-dideoxy-2-O-methyl-β-D-glucopyranosyl-(1->3)-2-O-acetyl-4-O-benzyl-α-L-rhamnopyranoside
CAS No.:870543-41-2
Molecular Formula:C₃₆H₄₃N₃O₁₀
Molecular Weight:677.752
Hs Code.:

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

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

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

There total 4 articles about 4-methoxyphenyl 4-azido-3-O-benzyl-4,6-dideoxy-2-O-methyl-β-D-glucopyranosyl-(1->3)-2-O-acetyl-4-O-benzyl-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: 73.0%

: 870543-50-3
Acetic acid (2S,3R,4R,5S,6S)-4-((2S,3R,4S,5R,6R)-5-azido-4-benzyloxy-3-hydroxy-6-methyl-tetrahydro-pyran-2-yloxy)-5-benzyloxy-2-(4-methoxy-phenoxy)-6-methyl-tetrahydro-pyran-3-yl ester

: 74-88-4
methyl iodide

: 870543-41-2
4-methoxyphenyl 4-azido-3-O-benzyl-4,6-dideoxy-2-O-methyl-β-D-glucopyranosyl-(1->3)-2-O-acetyl-4-O-benzyl-α-L-rhamnopyranoside

Guidance literature:: With dimethylsulfide; silver(l) oxide; In tetrahydrofuran; at 25 ℃; for 8h;
DOI:10.1002/anie.200502615

Reference yield:

: 74-88-4
methyl iodide

: 870543-41-2
4-methoxyphenyl 4-azido-3-O-benzyl-4,6-dideoxy-2-O-methyl-β-D-glucopyranosyl-(1->3)-2-O-acetyl-4-O-benzyl-α-L-rhamnopyranoside

Guidance literature:: 4-Oxo-pentanoic acid (2S,3R,4S,5R,6R)-2-[(2S,3R,4R,5S,6S)-3-acetoxy-5-benzyloxy-2-(4-methoxy-phenoxy)-6-methyl-tetrahydro-pyran-4-yloxy]-5-azido-4-benzyloxy-6-methyl-tetrahydro-pyran-3-yl ester; With hydrazinium monoacetate; In methanol; dichloromethane; at 25 ℃; for 12h;

methyl iodide; With silver(l) oxide; dimethylsulfide; In tetrahydrofuran; at 25 ℃; for 8h;

Reference yield:

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

: 870543-41-2
4-methoxyphenyl 4-azido-3-O-benzyl-4,6-dideoxy-2-O-methyl-β-D-glucopyranosyl-(1->3)-2-O-acetyl-4-O-benzyl-α-L-rhamnopyranoside

Guidance literature:: Multi-step reaction with 3 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

With dimethylsulfide; trimethylsilyl trifluoromethanesulfonate; hydrazinium monoacetate; silver(l) oxide; In tetrahydrofuran; methanol; dichloromethane;
DOI:10.1002/anie.200502615