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

Base Information

• Chemical Name: S-phenyl-2-O-benzyl-4,6-O-[1-cyano-2-(2-iodophenyl)]ethylidene-3-O-(2-naphthalenylmethyl)-1-thio-α-D-mannopyranoside
• CAS No.: 911811-33-1
• Molecular Formula: C₃₉H₃₄INO₅S
• Molecular Weight: 755.673
• Mol file: 911811-33-1.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 1 articles about S-phenyl-2-O-benzyl-4,6-O-[1-cyano-2-(2-iodophenyl)]ethylidene-3-O-(2-naphthalenylmethyl)-1-thio-α-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: 68.0%

triethyl 2-(2-iodophenyl)orthoacetate (887699-73-2) + phenyl 2-O-benzyl-3-O-(naphth-2-ylmethyl)-1-thio-α-D-mannopyranoside + trimethylsilyl cyanide (7677-24-9) → 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)

Guidance literature:

triethyl 2-(2-iodophenyl)orthoacetate; phenyl 2-O-benzyl-3-O-(naphth-2-ylmethyl)-1-thio-α-D-mannopyranoside; With camphor-10-sulfonic acid; 4-(2-iodophenyl)butanoic acid; In dichloromethane; at 0 ℃; for 4h;

trimethylsilyl cyanide; With boron trifluoride diethyl etherate; In dichloromethane; at 20 ℃;

DOI:10.1021/ol061706m

Reference yield:

1-cyclohexyl-2-O-benzyl-4,6-O-[1-cyano-2-(2-iodophenyl)]ethylidene-β-D-mannopyranoside (911811-34-2) + 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) → C61H60I2N2O11

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;

1-cyclohexyl-2-O-benzyl-4,6-O-[1-cyano-2-(2-iodophenyl)]ethylidene-β-D-mannopyranoside; In dichloromethane; at -70 ℃; for 1h;

DOI:10.1021/ol061706m

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) + 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 (911811-35-3) → C83H80I3N3O16

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;

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; In dichloromethane; at -78 ℃; for 1h;

DOI:10.1021/ol061706m

upstream raw materials:

triethyl 2-(2-iodophenyl)orthoacetate

trimethylsilyl cyanide

Downstream raw materials:

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

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

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