N-benzyloxycarbonyl-O-(2,3-di-O-benzyl-4,6-O-[1-cyano-2-(2-iodophenyl)]ethylidene-β-D-mannopyranosyl)-L-threonine methyl ester

Base Information

Chemical Name:N-benzyloxycarbonyl-O-(2,3-di-O-benzyl-4,6-O-[1-cyano-2-(2-iodophenyl)]ethylidene-β-D-mannopyranosyl)-L-threonine methyl ester
CAS No.:887699-89-0
Molecular Formula:C₄₂H₄₃IN₂O₁₀
Molecular Weight:862.715
Hs Code.:

Synonyms:N-benzyloxycarbonyl-O-(2,3-di-O-benzyl-4,6-O-[1-cyano-2-(2-iodophenyl)]ethylidene-β-D-mannopyranosyl)-L-threonine methyl ester

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Chemical Property of N-benzyloxycarbonyl-O-(2,3-di-O-benzyl-4,6-O-[1-cyano-2-(2-iodophenyl)]ethylidene-β-D-mannopyranosyl)-L-threonine methyl ester

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Technology Process of N-benzyloxycarbonyl-O-(2,3-di-O-benzyl-4,6-O-[1-cyano-2-(2-iodophenyl)]ethylidene-β-D-mannopyranosyl)-L-threonine methyl ester

There total 5 articles about N-benzyloxycarbonyl-O-(2,3-di-O-benzyl-4,6-O-[1-cyano-2-(2-iodophenyl)]ethylidene-β-D-mannopyranosyl)-L-threonine 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: 71.0%

: 887699-74-3
1-S-ethyl 2,3-di-O-benzyl-4,6-O-[1-cyano-2-(2-iodophenyl)]ethylidene-α-D-mannopyranoside

: 57224-63-2
methyl (2S,3R)-2-(benzyloxycarbonylamino)-3-hydroxybutyrate

: 887699-89-0
N-benzyloxycarbonyl-O-(2,3-di-O-benzyl-4,6-O-[1-cyano-2-(2-iodophenyl)]ethylidene-β-D-mannopyranosyl)-L-threonine methyl ester

Guidance literature:: 1-S-ethyl 2,3-di-O-benzyl-4,6-O-[1-cyano-2-(2-iodophenyl)]ethylidene-α-D-mannopyranoside; With trifluoromethylsulfonic anhydride; 1,1'-sulfinylbisbenzene; 2,4,5-tri-tert-butylpyrimidine; In dichloromethane; at -70 - -20 ℃; for 0.75h;

methyl (2S,3R)-2-(benzyloxycarbonylamino)-3-hydroxybutyrate; In dichloromethane; at -70 ℃; for 2h;
DOI:10.1021/jo0526688

Reference yield:

: 887699-73-2
triethyl 2-(2-iodophenyl)orthoacetate

: 887699-89-0
N-benzyloxycarbonyl-O-(2,3-di-O-benzyl-4,6-O-[1-cyano-2-(2-iodophenyl)]ethylidene-β-D-mannopyranosyl)-L-threonine methyl ester

Guidance literature:: Multi-step reaction with 3 steps

1.1: CSA / CH₂Cl₂ / 3 h / 20 °C

2.1: 0.931 g / BF₃*Et₂O / CH₂Cl₂ / 1.5 h / 20 °C

3.1: Ph₂SO; tri-tert-butyl-pyrimidine; triflic anhydride / CH₂Cl₂ / 0.75 h / -70 - -20 °C

3.2: 71 percent / CH₂Cl₂ / 2 h / -70 °C

With trifluoromethylsulfonic anhydride; 1,1'-sulfinylbisbenzene; 2,4,5-tri-tert-butylpyrimidine; camphor-10-sulfonic acid; boron trifluoride diethyl etherate; In dichloromethane;
DOI:10.1021/jo0526688

Reference yield:

: ethyl (2-iodophenyl)iminoacetate hydrochloride

: 887699-89-0
N-benzyloxycarbonyl-O-(2,3-di-O-benzyl-4,6-O-[1-cyano-2-(2-iodophenyl)]ethylidene-β-D-mannopyranosyl)-L-threonine methyl ester

Guidance literature:: Multi-step reaction with 4 steps

1.1: 48 h / 20 °C

2.1: CSA / CH₂Cl₂ / 3 h / 20 °C

3.1: 0.931 g / BF₃*Et₂O / CH₂Cl₂ / 1.5 h / 20 °C

4.1: Ph₂SO; tri-tert-butyl-pyrimidine; triflic anhydride / CH₂Cl₂ / 0.75 h / -70 - -20 °C

4.2: 71 percent / CH₂Cl₂ / 2 h / -70 °C

With trifluoromethylsulfonic anhydride; 1,1'-sulfinylbisbenzene; 2,4,5-tri-tert-butylpyrimidine; camphor-10-sulfonic acid; boron trifluoride diethyl etherate; In dichloromethane;
DOI:10.1021/jo0526688