β-1-deoxy-1-C-(phenylthio)-2-O-(1'-oxo-2'-diazo-2'-(methoxycarbonyl)ethyl)-3,4-O-isopropylidene-D-arabinopyranose

Base Information

• Chemical Name: β-1-deoxy-1-C-(phenylthio)-2-O-(1'-oxo-2'-diazo-2'-(methoxycarbonyl)ethyl)-3,4-O-isopropylidene-D-arabinopyranose
• CAS No.: 107961-26-2
• Molecular Formula: C₁₈H₂₀N₂O₇S
• Molecular Weight: 408.432
• Mol file: 107961-26-2.mol

Synonyms:β-1-deoxy-1-C-(phenylthio)-2-O-(1'-oxo-2'-diazo-2'-(methoxycarbonyl)ethyl)-3,4-O-isopropylidene-D-arabinopyranose

Chemical Property of β-1-deoxy-1-C-(phenylthio)-2-O-(1'-oxo-2'-diazo-2'-(methoxycarbonyl)ethyl)-3,4-O-isopropylidene-D-arabinopyranose

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of β-1-deoxy-1-C-(phenylthio)-2-O-(1'-oxo-2'-diazo-2'-(methoxycarbonyl)ethyl)-3,4-O-isopropylidene-D-arabinopyranose

There total 3 articles about β-1-deoxy-1-C-(phenylthio)-2-O-(1'-oxo-2'-diazo-2'-(methoxycarbonyl)ethyl)-3,4-O-isopropylidene-D-arabinopyranose 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: 85.0%

β-1-deoxy-1-C-(phenylthio)-2-O-(1'-oxo-2'-(methoxycarbonyl)ethyl)-3,4-O-isopropylidene-D-arabinopyranose (107961-25-1) → β-1-deoxy-1-C-(phenylthio)-2-O-(1'-oxo-2'-diazo-2'-(methoxycarbonyl)ethyl)-3,4-O-isopropylidene-D-arabinopyranose (107961-26-2)

Guidance literature:

With 4-toluenesulfonyl azide; triethylamine; In acetonitrile; for 4h; Ambient temperature;

DOI:10.1021/ja00244a024

Reference yield:

β-2-O-(1'-oxo-2'-(methoxycarbonyl)ethyl)-3,4-O-isopropylidene-D-arabinopyranose (107961-37-5) → β-1-deoxy-1-C-(phenylthio)-2-O-(1'-oxo-2'-diazo-2'-(methoxycarbonyl)ethyl)-3,4-O-isopropylidene-D-arabinopyranose (107961-26-2)

Guidance literature:

Multi-step reaction with 2 steps

1: 30.4 percent / tri-n-butylphosphine / CH₂Cl₂ / 3 h / Ambient temperature

2: 85 percent / Et₃N, p-toluenesulfonyl azide / acetonitrile / 4 h / Ambient temperature

With 4-toluenesulfonyl azide; tributylphosphine; triethylamine; In dichloromethane; acetonitrile;

DOI:10.1021/ja00244a024

Reference yield:

diphenyldisulfane (882-33-7) → β-1-deoxy-1-C-(phenylthio)-2-O-(1'-oxo-2'-diazo-2'-(methoxycarbonyl)ethyl)-3,4-O-isopropylidene-D-arabinopyranose (107961-26-2)

Guidance literature:

Multi-step reaction with 2 steps

1: 30.4 percent / tri-n-butylphosphine / CH₂Cl₂ / 3 h / Ambient temperature

2: 85 percent / Et₃N, p-toluenesulfonyl azide / acetonitrile / 4 h / Ambient temperature

With 4-toluenesulfonyl azide; tributylphosphine; triethylamine; In dichloromethane; acetonitrile;

DOI:10.1021/ja00244a024

upstream raw materials:

β-1-deoxy-1-C-(phenylthio)-2-O-(1'-oxo-2'-(methoxycarbonyl)ethyl)-3,4-O-isopropylidene-D-arabinopyranose

β-2-O-(1'-oxo-2'-(methoxycarbonyl)ethyl)-3,4-O-isopropylidene-D-arabinopyranose

diphenyldisulfane

Downstream raw materials:

[(3aS,5aR,8aR,8bS)-7,7-Dimethyl-tetrahydro-bis[1,3]dioxolo[4,5-b;4',5'-d]pyran-(2E)-ylidene]-phenylsulfanyl-acetic acid methyl ester

[(3aS,5aR,8aR,8bS)-7,7-Dimethyl-tetrahydro-bis[1,3]dioxolo[4,5-b;4',5'-d]pyran-(2Z)-ylidene]-phenylsulfanyl-acetic acid methyl ester

(3aR,5aS,9aS,9bR)-2,2-Dimethyl-8-oxo-6-phenyl-3a,4,5a,8,9a,9b-hexahydro-1,3,5,9-tetraoxa-6λ⁴-thia-cyclopenta[a]naphthalene-7-carboxylic acid methyl ester