phenyl 3,4,6-tri-O-benzyl-2-deoxy-2-iodo-1-thio-α-D-mannopyranoside

Base Information

• Chemical Name: phenyl 3,4,6-tri-O-benzyl-2-deoxy-2-iodo-1-thio-α-D-mannopyranoside
• CAS No.: 653575-98-5
• Molecular Formula: C₃₃H₃₃IO₄S
• Molecular Weight: 652.593
• Mol file: 653575-98-5.mol

Synonyms:phenyl 3,4,6-tri-O-benzyl-2-deoxy-2-iodo-1-thio-α-D-mannopyranoside

Chemical Property of phenyl 3,4,6-tri-O-benzyl-2-deoxy-2-iodo-1-thio-α-D-mannopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of phenyl 3,4,6-tri-O-benzyl-2-deoxy-2-iodo-1-thio-α-D-mannopyranoside

There total 7 articles about phenyl 3,4,6-tri-O-benzyl-2-deoxy-2-iodo-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: 61.0%

(E)-3,4,6-tri-O-benzyl-1,2-dideoxy-1-phenylsulfanyl-D-arabino-hex-1-enitol (653575-97-4) → phenyl 3,4,6-tri-O-benzyl-2-deoxy-2-iodo-1-thio-α-D-mannopyranoside (653575-98-5)

Guidance literature:

(E)-3,4,6-tri-O-benzyl-1,2-dideoxy-1-phenylsulfanyl-D-arabino-hex-1-enitol; With potassium hydride; In diethyl ether; at 0 ℃; for 0.5h;

With iodine; In diethyl ether; at -78 ℃; for 1h;

DOI:10.1055/s-2003-42066

Reference yield: 36.0%

3,4,6-tri-O-benzyl-1,2-dideoxy-1-phenylsulfanyl-D-arabino-hex-1-enitol → phenyl 3,4,6-tri-O-benzyl-2-deoxy-2-iodo-1-thio-α-D-mannopyranoside (653575-98-5)

Guidance literature:

With N-iodo-succinimide; sodium hydrogencarbonate; In acetonitrile; at 0 ℃; for 18h;

DOI:10.1021/jo051461b

Reference yield:

2,3,5-tri-O-benzyl-D-arabinofuranose (160549-10-0) → phenyl 3,4,6-tri-O-benzyl-2-deoxy-2-iodo-1-thio-α-D-mannopyranoside (653575-98-5)

Guidance literature:

Multi-step reaction with 2 steps

1: 23 percent / LDA / tetrahydrofuran / -78 - 20 °C

2: 61 percent / I₂; KH / diethyl ether / 1 h / -78 °C

With iodine; potassium hydride; lithium diisopropyl amide; In tetrahydrofuran; diethyl ether; 1: Wadsworth-Emmons reaction;

DOI:10.1021/jo051461b

upstream raw materials:

(E)-3,4,6-tri-O-benzyl-1,2-dideoxy-1-phenylsulfanyl-D-arabino-hex-1-enitol

diethyl [(phenylthio)methyl]phosphonate

(phenylsulfanylmethyl)trimethylsilane

2,3,5-tri-O-benzyl-D-arabinofuranose

Downstream raw materials:

cyclohexyl 3,4,6-tri-O-benzyl-2-deoxy-2-iodo-α-D-glucopyranoside

3,4,6-tri-O-benzyl-D-glucal