3-acetamido-3-deoxy-6-O-triphenylmethyl-D-mannose diethyl dithioacetal

Base Information

• Chemical Name: 3-acetamido-3-deoxy-6-O-triphenylmethyl-D-mannose diethyl dithioacetal
• CAS No.: 90706-21-1
• Molecular Formula: C₃₁H₃₉NO₅S₂
• Molecular Weight: 569.786
• Mol file: 90706-21-1.mol

Synonyms:3-acetamido-3-deoxy-6-O-triphenylmethyl-D-mannose diethyl dithioacetal

Chemical Property of 3-acetamido-3-deoxy-6-O-triphenylmethyl-D-mannose diethyl dithioacetal

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 3-acetamido-3-deoxy-6-O-triphenylmethyl-D-mannose diethyl dithioacetal

There total 8 articles about 3-acetamido-3-deoxy-6-O-triphenylmethyl-D-mannose 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:

trityl chloride (76-83-5) + N-[(1S,2S,3R)-1-((S)-2,2-Bis-ethylsulfanyl-1-hydroxy-ethyl)-2,3,4-trihydroxy-butyl]-acetamide (22617-60-3,22738-78-9) → 3-acetamido-3-deoxy-6-O-triphenylmethyl-D-mannose diethyl dithioacetal (90706-21-1)

Guidance literature:

With pyridine; Yield given;

DOI:10.1246/cl.1984.513

Reference yield:

methyl 3-acetamido-2,4,6-tri-O-acetyl-3-deoxy-α-D-mannopyranoside (72523-35-4) → 3-acetamido-3-deoxy-6-O-triphenylmethyl-D-mannose diethyl dithioacetal (90706-21-1)

Guidance literature:

Multi-step reaction with 3 steps

1: 1.) 2M HCl; 2.) pyridine / 1.) reflux, 13 h; 2.) overnight

2: 1.) sodium methoxide / 1.) MeOH, 2 h; 2.) conc. HCl, -15 deg C, 7 h

3: 4-dimethylaminopyridine / pyridine / 3.5 h / 70 °C

With pyridine; hydrogenchloride; dmap; sodium methylate; In pyridine;

DOI:10.1016/0008-6215(85)85186-7

Reference yield:

Methyl 3-acetamido-4,6-O-benzylidene-3-deoxy-α-D-glucopyranoside (17327-08-1) → 3-acetamido-3-deoxy-6-O-triphenylmethyl-D-mannose diethyl dithioacetal (90706-21-1)

Guidance literature:

Multi-step reaction with 6 steps

1: pyridine / 2.5 h

2: 97 percent / 0.5percent aq. HCl / methanol / 1 h / Heating

3: 1.) sodium acetate; 2.) pyridine / 1.) water, 2-methoxyethanol, 25 h, reflux; 2.) 3 h

4: 1.) 2M HCl; 2.) pyridine / 1.) reflux, 13 h; 2.) overnight

5: 1.) sodium methoxide / 1.) MeOH, 2 h; 2.) conc. HCl, -15 deg C, 7 h

6: 4-dimethylaminopyridine / pyridine / 3.5 h / 70 °C

With pyridine; hydrogenchloride; dmap; sodium methylate; sodium acetate; In pyridine; methanol;

DOI:10.1016/0008-6215(85)85186-7

upstream raw materials:

trityl chloride

N-[(1S,2S,3R)-1-((S)-2,2-Bis-ethylsulfanyl-1-hydroxy-ethyl)-2,3,4-trihydroxy-butyl]-acetamide

Methyl 3-acetamido-4,6-O-benzylidene-3-deoxy-α-D-glucopyranoside

methyl 3-acetamido-2,4,6-tri-O-acetyl-3-deoxy-α-D-mannopyranoside

Downstream raw materials:

swainsonine

3-acetamido-2,4,5-tri-O-benzyl-3-deoxy-6-O-tosyl-D-mannose diethyl dithioacetal

swainsonine tribenzylate

(1S,2R,8R,8aR)-1,2,8-tris(benzyloxy)hexahydroindolizin-5(1H)-one