methyl 2-benzyloxycarbonylamino-4,5-dehydro-2,4-dideoxy-3-O-methoxycarbonyl-6-O-tert-butyldimethylsilyl-α-D-glucopyranoside

Base Information

Chemical Name:methyl 2-benzyloxycarbonylamino-4,5-dehydro-2,4-dideoxy-3-O-methoxycarbonyl-6-O-tert-butyldimethylsilyl-α-D-glucopyranoside
CAS No.:1350556-20-5
Molecular Formula:C₂₃H₃₅NO₈Si
Molecular Weight:481.618
Hs Code.:

Synonyms:methyl 2-benzyloxycarbonylamino-4,5-dehydro-2,4-dideoxy-3-O-methoxycarbonyl-6-O-tert-butyldimethylsilyl-α-D-glucopyranoside

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Chemical Property of methyl 2-benzyloxycarbonylamino-4,5-dehydro-2,4-dideoxy-3-O-methoxycarbonyl-6-O-tert-butyldimethylsilyl-α-D-glucopyranoside

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Technology Process of methyl 2-benzyloxycarbonylamino-4,5-dehydro-2,4-dideoxy-3-O-methoxycarbonyl-6-O-tert-butyldimethylsilyl-α-D-glucopyranoside

There total 13 articles about methyl 2-benzyloxycarbonylamino-4,5-dehydro-2,4-dideoxy-3-O-methoxycarbonyl-6-O-tert-butyldimethylsilyl-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: 49.0%

: 1350556-15-8
methyl 6-formyl-2-benzyloxycarbonylamino-2-deoxy-3-O-methoxycarbonyl-α-D-glucopyranoside

: 133732-91-9
tert-butyldimethylsilyl triflate

: 1350556-20-5
methyl 2-benzyloxycarbonylamino-4,5-dehydro-2,4-dideoxy-3-O-methoxycarbonyl-6-O-tert-butyldimethylsilyl-α-D-glucopyranoside

Guidance literature:: With pyridine; L-Selectride; In tetrahydrofuran; at -78 - 0 ℃; for 0.333333h; Inert atmosphere;
DOI:10.1021/ol2027703

Reference yield: 49.0%

: 1350556-18-1
methyl 2-benzyloxycarbonylamino-4,5-dehydro-2,4-dideoxy-3-O-methoxycarbonyl-α-D-glucopyranoside

: 133732-91-9
tert-butyldimethylsilyl triflate

: 1350556-20-5
methyl 2-benzyloxycarbonylamino-4,5-dehydro-2,4-dideoxy-3-O-methoxycarbonyl-6-O-tert-butyldimethylsilyl-α-D-glucopyranoside

Guidance literature:: With pyridine; In dichloromethane; at -78 - 0 ℃; for 0.333333h; Inert atmosphere;
DOI:10.1021/ol2027703

Reference yield:

: 1350556-11-4
methyl 2-benzyloxycarbonylamino-2-deoxy-3-O-methoxycarbonyl-6-O-tert-butyldimethylsilyl-α-D-glucopyranoside

: 1350556-20-5
methyl 2-benzyloxycarbonylamino-4,5-dehydro-2,4-dideoxy-3-O-methoxycarbonyl-6-O-tert-butyldimethylsilyl-α-D-glucopyranoside

Guidance literature:: Multi-step reaction with 5 steps

1: triethylamine / dichloromethane / 3 h / 20 °C / Inert atmosphere

2: tetrabutyl ammonium fluoride; acetic acid / tetrahydrofuran / 16 h / 20 °C / Inert atmosphere

3: sulfur trioxide pyridine complex; triethylamine / dichloromethane; dimethyl sulfoxide / 3.25 h / 0 - 20 °C / Inert atmosphere

4: sodium tetrahydroborate; ethanol / tetrahydrofuran / 0.5 h / 0 °C / Inert atmosphere

5: pyridine / dichloromethane / 0.33 h / -78 - 0 °C / Inert atmosphere

With pyridine; sodium tetrahydroborate; ethanol; tetrabutyl ammonium fluoride; sulfur trioxide pyridine complex; acetic acid; triethylamine; In tetrahydrofuran; dichloromethane; dimethyl sulfoxide;
DOI:10.1021/ol2027703