methyl 3-O-benzyl-2-(N-benzyl-N-benzyloxycarbonylamino)-2-deoxy-α-D-glucopyranoside

Base Information

• Chemical Name: methyl 3-O-benzyl-2-(N-benzyl-N-benzyloxycarbonylamino)-2-deoxy-α-D-glucopyranoside
• CAS No.: 129095-44-9
• Molecular Formula: C₂₉H₃₃NO₇
• Molecular Weight: 507.584

Synonyms:methyl 3-O-benzyl-2-(N-benzyl-N-benzyloxycarbonylamino)-2-deoxy-α-D-glucopyranoside

Chemical Property of methyl 3-O-benzyl-2-(N-benzyl-N-benzyloxycarbonylamino)-2-deoxy-α-D-glucopyranoside

Chemical Property:

Purity/Quality:

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Technology Process of methyl 3-O-benzyl-2-(N-benzyl-N-benzyloxycarbonylamino)-2-deoxy-α-D-glucopyranoside

There total 4 articles about methyl 3-O-benzyl-2-(N-benzyl-N-benzyloxycarbonylamino)-2-deoxy-α-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:

benzyl ((2R,4aR,6S,7R,8R,8aS)-8-hydroxy-6-methoxy-2-phenyl hexahydropyrano[3,2-d][1,3]dioxin-7-yl)carbamate (93000-10-3) → methyl 3-O-benzyl-2-(N-benzyl-N-benzyloxycarbonylamino)-2-deoxy-α-D-glucopyranoside (129095-44-9)

Guidance literature:

Multi-step reaction with 2 steps

1: 75 percent / NaH / dimethylformamide / 3 h / Ambient temperature

2: aq. acetic acid / 3 h / Heating

With sodium hydride; acetic acid; In N,N-dimethyl-formamide;

DOI:10.1016/S0040-4020(01)97594-5

Reference yield:

benzyl bromide (100-39-0) → methyl 3-O-benzyl-2-(N-benzyl-N-benzyloxycarbonylamino)-2-deoxy-α-D-glucopyranoside (129095-44-9)

Guidance literature:

Multi-step reaction with 2 steps

1: 75 percent / NaH / dimethylformamide / 3 h / Ambient temperature

2: aq. acetic acid / 3 h / Heating

With sodium hydride; acetic acid; In N,N-dimethyl-formamide;

DOI:10.1016/S0040-4020(01)97594-5

Reference yield:

((2S,3R,4R,5S,6R)-4,5-Dihydroxy-6-hydroxymethyl-2-methoxy-tetrahydro-pyran-3-yl)-carbamic acid benzyl ester (4704-15-8) → methyl 3-O-benzyl-2-(N-benzyl-N-benzyloxycarbonylamino)-2-deoxy-α-D-glucopyranoside (129095-44-9)

Guidance literature:

Multi-step reaction with 3 steps

1: 85 percent / ZnCl₂ / 24 h

2: 75 percent / NaH / dimethylformamide / 3 h / Ambient temperature

3: aq. acetic acid / 3 h / Heating

With sodium hydride; acetic acid; zinc(II) chloride; In N,N-dimethyl-formamide;

DOI:10.1016/S0040-4020(01)97594-5

upstream raw materials:

methyl 4,6-O-benzylidene-3-O-benzyl-2-(N-benzyl-N-benzyloxycarbonyl-amino)-2-deoxy-α-D-glucopyranoside

benzyl ((2R,4aR,6S,7R,8R,8aS)-8-hydroxy-6-methoxy-2-phenyl hexahydropyrano[3,2-d][1,3]dioxin-7-yl)carbamate

benzyl bromide

((2S,3R,4R,5S,6R)-4,5-Dihydroxy-6-hydroxymethyl-2-methoxy-tetrahydro-pyran-3-yl)-carbamic acid benzyl ester

Downstream raw materials:

methyl 3-O-benzyl-2-(N-benzyl-N-benzyloxycarbonylamino)-2,6-dideoxy-6-iodo-α-D-glucopyranoside

1D-(1,2,4/3,5)-2-amino-1,2-N,O-carbonyl-4,7-benzylidene-5-C-hydroxymethyl-1,3,4-cyclohexanetriol

(R)-2-((3aS,4R,4aR,6R,8aR,9aS)-2-Oxo-6-phenyl-octahydro-1,5,7-trioxa-3-aza-cyclopenta[b]naphthalen-4-yloxy)-propionic acid

1D-(1,2/3)-3-O-benzyl-2-benzylamino-1,2-N,O-carbonyl-5-C-hydroxy-methyl-cyclohex-4-en-1,3-diol

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