(-)-1,6-dideoxy-2,5-di-O-benzyl-3,4-O-isopropylidene-1,6-thio-L-iditol

Base Information

• Chemical Name: (-)-1,6-dideoxy-2,5-di-O-benzyl-3,4-O-isopropylidene-1,6-thio-L-iditol
• CAS No.: 266682-77-3
• Molecular Formula: C₂₃H₂₈O₄S
• Molecular Weight: 400.539
• Mol file: 266682-77-3.mol

Synonyms:(-)-1,6-dideoxy-2,5-di-O-benzyl-3,4-O-isopropylidene-1,6-thio-L-iditol

Chemical Property of (-)-1,6-dideoxy-2,5-di-O-benzyl-3,4-O-isopropylidene-1,6-thio-L-iditol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (-)-1,6-dideoxy-2,5-di-O-benzyl-3,4-O-isopropylidene-1,6-thio-L-iditol

There total 1 articles about (-)-1,6-dideoxy-2,5-di-O-benzyl-3,4-O-isopropylidene-1,6-thio-L-iditol 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:

benzyl bromide (100-39-0) + 1,6-thioanhydro-3,4-O-isopropylidene-L-iditol (63699-95-6) → (-)-1,6-dideoxy-2,5-di-O-benzyl-3,4-O-isopropylidene-1,6-thio-L-iditol (266682-77-3)

Guidance literature:

With sodium hydride; potassium iodide; In tetrahydrofuran; for 19h;

DOI:10.1016/S0040-4020(00)00011-9

Reference yield: 90.0%

(-)-1,6-dideoxy-2,5-di-O-benzyl-3,4-O-isopropylidene-1,6-thio-L-iditol (266682-77-3) → (-)-1,6-dideoxy-2,5-di-O-benzyl-3,4-O-isopropylidene-1,6-thio-L-iditol-S,S-dioxide (266682-74-0)

Guidance literature:

With 3-chloro-benzenecarboperoxoic acid; In dichloromethane; at 20 ℃; for 4h;

DOI:10.1016/S0040-4020(00)00011-9

Reference yield:

(-)-1,6-dideoxy-2,5-di-O-benzyl-3,4-O-isopropylidene-1,6-thio-L-iditol (266682-77-3) → (3aR,4S,7S,7aR)-3a,4,7,7a-tetrahydro-2,2-dimethyl-4,7-di-O-benzyl-2,3-benzodioxole-4,7-diol (266682-75-1)

Guidance literature:

Multi-step reaction with 2 steps

1: 90 percent / m-chloroperbenzoic acid / CH₂Cl₂ / 4 h / 20 °C

2: 35 percent / KOH / 2-methyl-propan-2-ol; CCl₄; H₂O / 1 h / 20 °C

With potassium hydroxide; 3-chloro-benzenecarboperoxoic acid; In tetrachloromethane; dichloromethane; water; tert-butyl alcohol; 1: Oxidation / 2: Ramberg-Baecklung reaction;

DOI:10.1016/S0040-4020(00)00011-9

upstream raw materials:

benzyl bromide

1,6-thioanhydro-3,4-O-isopropylidene-L-iditol

Downstream raw materials:

(-)-1,6-dideoxy-2,5-di-O-benzyl-3,4-O-isopropylidene-1,6-thio-L-iditol-S,S-dioxide

(3aR,4S,7S,7aR)-3a,4,7,7a-tetrahydro-2,2-dimethyl-4,7-di-O-benzyl-2,3-benzodioxole-4,7-diol