methyl 4-O-(2,3-di-O-benzyl-4,6-O-[1-cyano-2-(2-iodophenyl)]ethylidene-β-D-mannopyranosyl)-2,3-O-isopropylidene-α-L-rhamnopyranoside

Base Information

Chemical Name:methyl 4-O-(2,3-di-O-benzyl-4,6-O-[1-cyano-2-(2-iodophenyl)]ethylidene-β-D-mannopyranosyl)-2,3-O-isopropylidene-α-L-rhamnopyranoside
CAS No.:887699-75-4
Molecular Formula:C₃₉H₄₄INO₁₀
Molecular Weight:813.684
Hs Code.:

Synonyms:methyl 4-O-(2,3-di-O-benzyl-4,6-O-[1-cyano-2-(2-iodophenyl)]ethylidene-β-D-mannopyranosyl)-2,3-O-isopropylidene-α-L-rhamnopyranoside

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Chemical Property of methyl 4-O-(2,3-di-O-benzyl-4,6-O-[1-cyano-2-(2-iodophenyl)]ethylidene-β-D-mannopyranosyl)-2,3-O-isopropylidene-α-L-rhamnopyranoside

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Technology Process of methyl 4-O-(2,3-di-O-benzyl-4,6-O-[1-cyano-2-(2-iodophenyl)]ethylidene-β-D-mannopyranosyl)-2,3-O-isopropylidene-α-L-rhamnopyranoside

There total 5 articles about methyl 4-O-(2,3-di-O-benzyl-4,6-O-[1-cyano-2-(2-iodophenyl)]ethylidene-β-D-mannopyranosyl)-2,3-O-isopropylidene-α-L-rhamnopyranoside 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: 92.0%

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

: 14133-63-2
methyl 2,3-O-isopropylidene-α-L-rhamnoside

: 887699-75-4
methyl 4-O-(2,3-di-O-benzyl-4,6-O-[1-cyano-2-(2-iodophenyl)]ethylidene-β-D-mannopyranosyl)-2,3-O-isopropylidene-α-L-rhamnopyranoside

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 2,3-O-isopropylidene-α-L-rhamnoside; In dichloromethane; at -70 ℃; for 2h;
DOI:10.1021/jo0526688

Reference yield:

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

: 887699-75-4
methyl 4-O-(2,3-di-O-benzyl-4,6-O-[1-cyano-2-(2-iodophenyl)]ethylidene-β-D-mannopyranosyl)-2,3-O-isopropylidene-α-L-rhamnopyranoside

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: 92 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

: 887699-75-4
methyl 4-O-(2,3-di-O-benzyl-4,6-O-[1-cyano-2-(2-iodophenyl)]ethylidene-β-D-mannopyranosyl)-2,3-O-isopropylidene-α-L-rhamnopyranoside

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: 92 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