methyl 2-benzyloxycarbonylamino-3,4-dehydro-2,3,4-trideoxy-6-O-tert-butyldimethylsilyl-α-D-glucopyranoside

Base Information

Chemical Name:methyl 2-benzyloxycarbonylamino-3,4-dehydro-2,3,4-trideoxy-6-O-tert-butyldimethylsilyl-α-D-glucopyranoside
CAS No.:1350556-22-7
Molecular Formula:C₂₁H₃₃NO₅Si
Molecular Weight:407.582
Hs Code.:

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

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

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

There total 16 articles about methyl 2-benzyloxycarbonylamino-3,4-dehydro-2,3,4-trideoxy-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: 85.0%

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

: 1350556-22-7
methyl 2-benzyloxycarbonylamino-3,4-dehydro-2,3,4-trideoxy-6-O-tert-butyldimethylsilyl-α-D-glucopyranoside

Guidance literature:: With tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; formic acid; tributylphosphine; triethylamine; In tetrahydrofuran; at -78 - 60 ℃; for 24h; Inert atmosphere; Sonication;
DOI:10.1021/ol2027703

Reference yield: 57.0%

: C₂₈H₃₇NO₇Si

: 1350556-22-7
methyl 2-benzyloxycarbonylamino-3,4-dehydro-2,3,4-trideoxy-6-O-tert-butyldimethylsilyl-α-D-glucopyranoside

Guidance literature:: With tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; formic acid; tributylphosphine; triethylamine; In tetrahydrofuran; at 60 ℃; for 36h; Inert atmosphere;
DOI:10.1021/ol2027703

Reference yield:

: 3006-58-4,13030-01-8,42890-10-8,42973-23-9,77059-32-6,121785-09-9,7474-40-0
2-carbobenzyloxyamino-2-deoxy-D-glucopyranose

: 1350556-22-7
methyl 2-benzyloxycarbonylamino-3,4-dehydro-2,3,4-trideoxy-6-O-tert-butyldimethylsilyl-α-D-glucopyranoside

Guidance literature:: Multi-step reaction with 11 steps

1: acetyl chloride / 24 h / 20 °C / Inert atmosphere

2: formic acid / 24 h / 20 °C / Inert atmosphere

3: pyridine / 1 h / 0 - 20 °C / Inert atmosphere

4: acetic acid / dichloromethane / 16 h / 60 °C / Inert atmosphere

5: dmap; triethylamine / dichloromethane / 16 h / 0 - 20 °C / Inert atmosphere

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

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

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

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

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

11: tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; formic acid; tributylphosphine; triethylamine / tetrahydrofuran / 24 h / -78 - 60 °C / Inert atmosphere; Sonication

With pyridine; dmap; sodium tetrahydroborate; tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; formic acid; ethanol; tributylphosphine; tetrabutyl ammonium fluoride; sulfur trioxide pyridine complex; acetic acid; triethylamine; acetyl chloride; In tetrahydrofuran; dichloromethane; dimethyl sulfoxide;
DOI:10.1021/ol2027703