1-cyclohexyl-2-O-benzyl-4,6-O-[1-cyano-2-(2-iodophenyl)]ethylidene-3-O-(2-naphthalenylmethyl)-β-D-mannopyranoside

Base Information

• Chemical Name: 1-cyclohexyl-2-O-benzyl-4,6-O-[1-cyano-2-(2-iodophenyl)]ethylidene-3-O-(2-naphthalenylmethyl)-β-D-mannopyranoside
• CAS No.: 911811-31-9
• Molecular Formula: C₃₉H₄₀INO₆
• Molecular Weight: 745.654
• Mol file: 911811-31-9.mol

Synonyms:1-cyclohexyl-2-O-benzyl-4,6-O-[1-cyano-2-(2-iodophenyl)]ethylidene-3-O-(2-naphthalenylmethyl)-β-D-mannopyranoside

Chemical Property of 1-cyclohexyl-2-O-benzyl-4,6-O-[1-cyano-2-(2-iodophenyl)]ethylidene-3-O-(2-naphthalenylmethyl)-β-D-mannopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 1-cyclohexyl-2-O-benzyl-4,6-O-[1-cyano-2-(2-iodophenyl)]ethylidene-3-O-(2-naphthalenylmethyl)-β-D-mannopyranoside

There total 3 articles about 1-cyclohexyl-2-O-benzyl-4,6-O-[1-cyano-2-(2-iodophenyl)]ethylidene-3-O-(2-naphthalenylmethyl)-β-D-mannopyranoside 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:

S-phenyl-2-O-benzyl-4,6-O-[1-cyano-2-(2-iodophenyl)]ethylidene-3-O-(2-naphthalenylmethyl)-1-thio-α-D-mannopyranoside (911811-33-1) + cyclohexanol (108-93-0) → 1-cyclohexyl-2-O-benzyl-4,6-O-[1-cyano-2-(2-iodophenyl)]ethylidene-3-O-(2-naphthalenylmethyl)-β-D-mannopyranoside (911811-31-9) + 1-cyclohexyl-2-O-benzyl-4,6-O-[1-cyano-2-(2-iodophenyl)]ethylidene-3-O-(2-naphthalenylmethyl)-α-D-mannopyranoside

Guidance literature:

S-phenyl-2-O-benzyl-4,6-O-[1-cyano-2-(2-iodophenyl)]ethylidene-3-O-(2-naphthalenylmethyl)-1-thio-α-D-mannopyranoside; With trifluoromethylsulfonic anhydride; 1,1'-sulfinylbisbenzene; 3 A molecular sieve; In dichloromethane; at -70 - -20 ℃; for 0.75h;

cyclohexanol; In dichloromethane; at -70 ℃; for 1h;

DOI:10.1021/ol061706m

Reference yield:

triethyl 2-(2-iodophenyl)orthoacetate (887699-73-2) → 1-cyclohexyl-2-O-benzyl-4,6-O-[1-cyano-2-(2-iodophenyl)]ethylidene-3-O-(2-naphthalenylmethyl)-β-D-mannopyranoside (911811-31-9)

Guidance literature:

Multi-step reaction with 2 steps

1.1: CSA; 2-(2-iodophenyl)-ethylacetate / CH₂Cl₂ / 4 h / 0 °C

1.2: 68 percent / BF₃*OEt₂ / CH₂Cl₂ / 20 °C

2.1: diphenyl sulfoxide; TTBP; triflic anhydride / molecular sieves 3 Angstroem / CH₂Cl₂ / 0.75 h / -70 - -20 °C

2.2: CH₂Cl₂ / 1 h / -70 °C

With trifluoromethylsulfonic anhydride; 1,1'-sulfinylbisbenzene; camphor-10-sulfonic acid; 4-(2-iodophenyl)butanoic acid; 3 A molecular sieve; In dichloromethane;

DOI:10.1021/ol061706m

Reference yield:

phenyl 2-O-benzyl-3-O-(naphth-2-ylmethyl)-1-thio-α-D-mannopyranoside → 1-cyclohexyl-2-O-benzyl-4,6-O-[1-cyano-2-(2-iodophenyl)]ethylidene-3-O-(2-naphthalenylmethyl)-β-D-mannopyranoside (911811-31-9)

Guidance literature:

Multi-step reaction with 2 steps

1.1: CSA; 2-(2-iodophenyl)-ethylacetate / CH₂Cl₂ / 4 h / 0 °C

1.2: 68 percent / BF₃*OEt₂ / CH₂Cl₂ / 20 °C

2.1: diphenyl sulfoxide; TTBP; triflic anhydride / molecular sieves 3 Angstroem / CH₂Cl₂ / 0.75 h / -70 - -20 °C

2.2: CH₂Cl₂ / 1 h / -70 °C

With trifluoromethylsulfonic anhydride; 1,1'-sulfinylbisbenzene; camphor-10-sulfonic acid; 4-(2-iodophenyl)butanoic acid; 3 A molecular sieve; In dichloromethane;

DOI:10.1021/ol061706m

upstream raw materials:

S-phenyl-2-O-benzyl-4,6-O-[1-cyano-2-(2-iodophenyl)]ethylidene-3-O-(2-naphthalenylmethyl)-1-thio-α-D-mannopyranoside

cyclohexanol

triethyl 2-(2-iodophenyl)orthoacetate

Downstream raw materials:

cyclohexyl-2-O-benzyl-4,6-O-[1-cyano-2-(2-iodophenyl)]ethylidene-β-D-mannopyranosyl-(1->3)-2-O-benzyl-4,6-O-[1-cyano-2-(2-iodophenyl)]ethylidene-β-D-mannopyranoside

1-cyclohexyl-2-O-benzyl-4,6-O-[1-cyano-2-(2-iodophenyl)]ethylidene-β-D-mannopyranoside