tert-butyldiphenylsilyl 4-(N-benzyloxycarbonylamino)-2-azido-3-O-chloroacetyl-2,4,6-trideoxy-β-D-galactopyranoside

Base Information

Chemical Name:tert-butyldiphenylsilyl 4-(N-benzyloxycarbonylamino)-2-azido-3-O-chloroacetyl-2,4,6-trideoxy-β-D-galactopyranoside
CAS No.:1271132-05-8
Molecular Formula:C₃₂H₃₇ClN₄O₆Si
Molecular Weight:637.207
Hs Code.:

Synonyms:tert-butyldiphenylsilyl 4-(N-benzyloxycarbonylamino)-2-azido-3-O-chloroacetyl-2,4,6-trideoxy-β-D-galactopyranoside

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Chemical Property of tert-butyldiphenylsilyl 4-(N-benzyloxycarbonylamino)-2-azido-3-O-chloroacetyl-2,4,6-trideoxy-β-D-galactopyranoside

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Technology Process of tert-butyldiphenylsilyl 4-(N-benzyloxycarbonylamino)-2-azido-3-O-chloroacetyl-2,4,6-trideoxy-β-D-galactopyranoside

There total 9 articles about tert-butyldiphenylsilyl 4-(N-benzyloxycarbonylamino)-2-azido-3-O-chloroacetyl-2,4,6-trideoxy-β-D-galactopyranoside 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: 100.0%

: 1271131-90-8
tert-butyldiphenylsilyl 4-(N-benzyloxycarbonylamino)-2-azido-2,4,6-trideoxy-β-D-galactopyranoside

: 541-88-8
Chloroacetic anhydride

: 1271132-05-8
tert-butyldiphenylsilyl 4-(N-benzyloxycarbonylamino)-2-azido-3-O-chloroacetyl-2,4,6-trideoxy-β-D-galactopyranoside

Guidance literature:: With pyridine; In dichloromethane; for 1h;
DOI:10.1021/jo102363d

Reference yield:

: 1384556-69-7
tert-butyldiphenylsilyl 2-azido-2,6-dideoxy-6-iodo-β-D-glucopyranoside

: 1271132-05-8
tert-butyldiphenylsilyl 4-(N-benzyloxycarbonylamino)-2-azido-3-O-chloroacetyl-2,4,6-trideoxy-β-D-galactopyranoside

Guidance literature:: Multi-step reaction with 5 steps

1.1: sodium cyanoborohydride / diethylene glycol dimethyl ether / 7 h / Reflux

2.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / dichloromethane / 1 h / -13 °C / Molecular sieve

2.2: -30 - 20 °C / Molecular sieve

2.3: 20 °C / Molecular sieve

3.1: acetic acid / water; ethyl acetate / 20 °C

4.1: triethylamine / dichloromethane / 0.75 h

5.1: pyridine / dichloromethane / 1 h

With pyridine; sodium cyanoborohydride; acetic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; In dichloromethane; diethylene glycol dimethyl ether; water; ethyl acetate;
DOI:10.1016/j.carres.2012.02.015

Reference yield:

: 2-azido-2-deoxy-D-glucose

: 1271132-05-8
tert-butyldiphenylsilyl 4-(N-benzyloxycarbonylamino)-2-azido-3-O-chloroacetyl-2,4,6-trideoxy-β-D-galactopyranoside

Guidance literature:: Multi-step reaction with 11 steps

1.1: pyridine / 20 °C

2.1: piperidine / tetrahydrofuran / 2.5 h

3.1: 1H-imidazole / N,N-dimethyl-formamide / 2 h / 60 °C

4.1: sodium methylate / methanol; dichloromethane

5.1: pyridine / 2 h / 0 °C

6.1: sodium iodide / butanone / 6 h / Reflux

7.1: sodium cyanoborohydride / diethylene glycol dimethyl ether / 7 h / Reflux

8.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / dichloromethane / 1 h / -13 °C / Molecular sieve

8.2: -30 - 20 °C / Molecular sieve

8.3: 20 °C / Molecular sieve

9.1: acetic acid / water; ethyl acetate / 20 °C

10.1: triethylamine / dichloromethane / 0.75 h

11.1: pyridine / dichloromethane / 1 h

With piperidine; pyridine; 1H-imidazole; sodium methylate; sodium cyanoborohydride; acetic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; sodium iodide; In tetrahydrofuran; pyridine; methanol; dichloromethane; diethylene glycol dimethyl ether; water; ethyl acetate; N,N-dimethyl-formamide; butanone;
DOI:10.1016/j.carres.2012.02.015