4-O-benzyl-6-bromo-6-deoxy-2,3-O-isopropylidene-D-glucose diethyl dithioacetal

Base Information

• Chemical Name: 4-O-benzyl-6-bromo-6-deoxy-2,3-O-isopropylidene-D-glucose diethyl dithioacetal
• CAS No.: 359642-15-2
• Molecular Formula: C₂₀H₃₁BrO₄S₂
• Molecular Weight: 479.5
• Mol file: 359642-15-2.mol

Synonyms:4-O-benzyl-6-bromo-6-deoxy-2,3-O-isopropylidene-D-glucose diethyl dithioacetal

Chemical Property of 4-O-benzyl-6-bromo-6-deoxy-2,3-O-isopropylidene-D-glucose diethyl dithioacetal

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 4-O-benzyl-6-bromo-6-deoxy-2,3-O-isopropylidene-D-glucose diethyl dithioacetal

There total 2 articles about 4-O-benzyl-6-bromo-6-deoxy-2,3-O-isopropylidene-D-glucose diethyl dithioacetal 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%

4-O-benzyl-2,3-O-isopropylidene-D-glucose diethyl dithioacetal (359642-14-1) → 4-O-benzyl-6-bromo-6-deoxy-2,3-O-isopropylidene-D-glucose diethyl dithioacetal (359642-15-2)

Guidance literature:

With carbon tetrabromide; triphenylphosphine; In tetrahydrofuran; at 20 ℃; for 0.75h;

DOI:10.1016/S0008-6215(01)00116-1

Reference yield:

4-O-benzyl-2,3:5,6-di-O-isopropylidene-D-glucose diethyl dithioacetal (149557-49-3) → 4-O-benzyl-6-bromo-6-deoxy-2,3-O-isopropylidene-D-glucose diethyl dithioacetal (359642-15-2)

Guidance literature:

Multi-step reaction with 2 steps

1: 70 percent / AcOH / H₂O / 20 °C

2: 61 percent / PPh₃; CBr₄ / tetrahydrofuran / 0.75 h / 20 °C

With carbon tetrabromide; acetic acid; triphenylphosphine; In tetrahydrofuran; water;

DOI:10.1016/S0008-6215(01)00116-1

Reference yield: 51.0%

acetic anhydride (108-24-7) + 4-O-benzyl-6-bromo-6-deoxy-2,3-O-isopropylidene-D-glucose diethyl dithioacetal (359642-15-2) → 5-O-acetyl-4-O-benzyl-6-bromo-6-deoxy-2,3-O-isopropylidene-D-glucose diethyl dithioacetal (359642-16-3)

Guidance literature:

With pyridine; at 20 ℃;

DOI:10.1016/S0008-6215(01)00116-1

upstream raw materials:

4-O-benzyl-2,3-O-isopropylidene-D-glucose diethyl dithioacetal

4-O-benzyl-2,3:5,6-di-O-isopropylidene-D-glucose diethyl dithioacetal

Downstream raw materials:

5-O-acetyl-4-O-benzyl-6-bromo-6-deoxy-2,3-O-isopropylidene-D-glucose diethyl dithioacetal

Acetic acid (1S,2S)-2-benzyloxy-1-bromomethyl-2-((4S,5R)-5-formyl-2,2-dimethyl-[1,3]dioxolan-4-yl)-ethyl ester

methyl 7-O-acetyl-4-O-benzyl-8-bromo-2,3,8-trideoxy-4,5-O-isopropylidene-D-gluco-oct-2-enonate

1L(1,2,4/3,5)-1-O-acetyl-2-O-benzyl-3,4-O-isopropylidene-5-C-methoxycarbonylmethylcyclohexan-1,2,3,4-tetrol