(E)-3,4:6,7-di-O-isopropylidene-1,2-dideoxy-1-phenylsulfanyl-D-manno-hept-1-enitol

Base Information

• Chemical Name: (E)-3,4:6,7-di-O-isopropylidene-1,2-dideoxy-1-phenylsulfanyl-D-manno-hept-1-enitol
• CAS No.: 871948-11-7
• Molecular Formula: C₁₉H₂₆O₅S
• Molecular Weight: 366.478
• Mol file: 871948-11-7.mol

Synonyms:(E)-3,4:6,7-di-O-isopropylidene-1,2-dideoxy-1-phenylsulfanyl-D-manno-hept-1-enitol

Chemical Property of (E)-3,4:6,7-di-O-isopropylidene-1,2-dideoxy-1-phenylsulfanyl-D-manno-hept-1-enitol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (E)-3,4:6,7-di-O-isopropylidene-1,2-dideoxy-1-phenylsulfanyl-D-manno-hept-1-enitol

There total 5 articles about (E)-3,4:6,7-di-O-isopropylidene-1,2-dideoxy-1-phenylsulfanyl-D-manno-hept-1-enitol 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:

2,3,5,6-di-O-isopropylidene-D-mannofuranose (7757-38-2,14131-84-1,23262-78-4,27108-13-0,33823-04-0,34685-42-2,57819-52-0,78039-08-4,78039-12-0,78964-16-6,94842-76-9,149342-31-4) + diphenyl(phenylthiomethyl)phosphine oxide (31238-57-0) → (Z)-3,4:6,7-di-O-isopropylidene-1,2-dideoxy-1-phenylsulfanyl-D-manno-hept-1-enitol + (E)-3,4:6,7-di-O-isopropylidene-1,2-dideoxy-1-phenylsulfanyl-D-manno-hept-1-enitol (871948-11-7)

Guidance literature:

diphenyl(phenylthiomethyl)phosphine oxide; With n-butyllithium; In tetrahydrofuran; hexane; at -78 ℃; for 0.5h;

2,3,5,6-di-O-isopropylidene-D-mannofuranose; In tetrahydrofuran; hexane; at 20 ℃; for 21h;

DOI:10.1021/jo051461b

Reference yield:

phenylthiomethyl triphenylphosphonium chloride (13884-92-9) → (E)-3,4:6,7-di-O-isopropylidene-1,2-dideoxy-1-phenylsulfanyl-D-manno-hept-1-enitol (871948-11-7)

Guidance literature:

Multi-step reaction with 2 steps

1: n-butyllithium / hexane; tetrahydrofuran / 0.5 h / 20 °C

2: hexane; tetrahydrofuran / 48 h / 20 °C

With n-butyllithium; In tetrahydrofuran; hexane;

DOI:10.1016/j.tet.2003.12.040

Reference yield:

1,2-dideoxy-3,4:5,7-di-O-isopropylidene-1-phenylthio-D-manno-hept-1-enitol → (Z)-3,4:6,7-di-O-isopropylidene-1,2-dideoxy-1-phenylsulfanyl-D-manno-hept-1-enitol + (E)-3,4:6,7-di-O-isopropylidene-1,2-dideoxy-1-phenylsulfanyl-D-manno-hept-1-enitol (871948-11-7)

Guidance literature:

With hydrogenchloride; In chloroform-d1; Title compound not separated from byproducts.;

DOI:10.1016/j.tet.2003.12.040

upstream raw materials:

2,3,5,6-di-O-isopropylidene-D-mannofuranose

(phenylthio)-methylenetriphenylphosphorane

diethyl [(phenylthio)methyl]phosphonate

diphenyl(phenylthiomethyl)phosphine oxide

Downstream raw materials:

phenyl 2-deoxy-2-iodo-3,4:6,7-di-O-isopropylidene-1-thio-D-glycero-α-D-taloheptopyranoside

(3aR,4R,7aR)-4-((R)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-2,2-dimethyl-3a,7a-dihydro-4H-[1,3]dioxolo[4,5-c]pyran