N-(benzyloxycarbonyl)-O-(4-O-acetyl-2-azido-3-O-chloroacetyl-2-deoxy-6-O-t-butyldiphenylsilyl-α-D-galactopyranosyl)-L-serine methyl ester

Base Information

Chemical Name:N-(benzyloxycarbonyl)-O-(4-O-acetyl-2-azido-3-O-chloroacetyl-2-deoxy-6-O-t-butyldiphenylsilyl-α-D-galactopyranosyl)-L-serine methyl ester
CAS No.:1447946-82-8
Molecular Formula:C₃₈H₄₅ClN₄O₁₁Si
Molecular Weight:797.334
Hs Code.:

Synonyms:N-(benzyloxycarbonyl)-O-(4-O-acetyl-2-azido-3-O-chloroacetyl-2-deoxy-6-O-t-butyldiphenylsilyl-α-D-galactopyranosyl)-L-serine methyl ester

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Chemical Property of N-(benzyloxycarbonyl)-O-(4-O-acetyl-2-azido-3-O-chloroacetyl-2-deoxy-6-O-t-butyldiphenylsilyl-α-D-galactopyranosyl)-L-serine methyl ester

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Technology Process of N-(benzyloxycarbonyl)-O-(4-O-acetyl-2-azido-3-O-chloroacetyl-2-deoxy-6-O-t-butyldiphenylsilyl-α-D-galactopyranosyl)-L-serine methyl ester

There total 15 articles about N-(benzyloxycarbonyl)-O-(4-O-acetyl-2-azido-3-O-chloroacetyl-2-deoxy-6-O-t-butyldiphenylsilyl-α-D-galactopyranosyl)-L-serine methyl ester 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: 74.0%

: 1676-81-9
N-benzyloxycarbonyl-L-serine methyl ester

: 1447946-79-3
phenyl 4-O-acetyl-2-azido-3-O-chloroacetyl-2-deoxy-6-O-t-butyldiphenylsilyl-1-thio-β-D-galactopyranoside

: 1447946-82-8
N-(benzyloxycarbonyl)-O-(4-O-acetyl-2-azido-3-O-chloroacetyl-2-deoxy-6-O-t-butyldiphenylsilyl-α-D-galactopyranosyl)-L-serine methyl ester

Guidance literature:: phenyl 4-O-acetyl-2-azido-3-O-chloroacetyl-2-deoxy-6-O-t-butyldiphenylsilyl-1-thio-β-D-galactopyranoside; With trifluoromethylsulfonic anhydride; 1,1'-sulfinylbisbenzene; In dichloromethane; at -60 ℃; for 0.166667h; Inert atmosphere;

N-benzyloxycarbonyl-L-serine methyl ester; In dichloromethane; at 1 ℃; for 1h; Inert atmosphere;
DOI:10.1039/c3ob40935j

Reference yield:

: 1676-81-9
N-benzyloxycarbonyl-L-serine methyl ester

: C₂₆H₃₁ClIN₃O₆Si

: 1447946-82-8
N-(benzyloxycarbonyl)-O-(4-O-acetyl-2-azido-3-O-chloroacetyl-2-deoxy-6-O-t-butyldiphenylsilyl-α-D-galactopyranosyl)-L-serine methyl ester

Guidance literature:: With iodine; In dichloromethane; at 20 ℃; for 6h; Inert atmosphere; Molecular sieve;
DOI:10.1039/c4ra12631a

Reference yield:

: 58479-61-1
tert-butylchlorodiphenylsilane

: 1447946-82-8
N-(benzyloxycarbonyl)-O-(4-O-acetyl-2-azido-3-O-chloroacetyl-2-deoxy-6-O-t-butyldiphenylsilyl-α-D-galactopyranosyl)-L-serine methyl ester

Guidance literature:: Multi-step reaction with 7 steps

1.1: pyridine / 12 h / Inert atmosphere

2.1: dimethyltin dichloride; N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 0.03 h / Inert atmosphere

2.2: 1.5 h / 20 °C / Inert atmosphere

3.1: pyridine / dichloromethane / 2 h / 10 °C / Inert atmosphere

4.1: tetrabutylammoniun azide / acetonitrile / 20 h / -30 °C / Inert atmosphere

5.1: water / acetonitrile / 1 h / 65 °C / Inert atmosphere

6.1: pyridine / dichloromethane / 0.5 h / 0 °C / Inert atmosphere

7.1: trifluoromethylsulfonic anhydride; 1,1'-sulfinylbisbenzene / dichloromethane / 0.17 h / -60 °C / Inert atmosphere

7.2: 1 h / 1 °C / Inert atmosphere

With pyridine; trifluoromethylsulfonic anhydride; 1,1'-sulfinylbisbenzene; water; dimethyltin dichloride; tetrabutylammoniun azide; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; dichloromethane; acetonitrile;
DOI:10.1039/c3ob40935j