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

Base Information

Chemical Name:3-acetamido-2,4,5-tri-O-benzyl-3-deoxy-6-O-tosyl-D-mannose diethyl dithioacetal
CAS No.:90706-23-3
Molecular Formula:C₄₀H₄₉NO₇S₃
Molecular Weight:752.03
Hs Code.:

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

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

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

There total 10 articles about 3-acetamido-2,4,5-tri-O-benzyl-3-deoxy-6-O-tosyl-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: 77.0%

: 90706-22-2
3-acetamido-2,4,5-tri-O-benzyl-3-deoxy-D-mannose diethyl dithioacetal

: 98-59-9
p-toluenesulfonyl chloride

: 90706-23-3
3-acetamido-2,4,5-tri-O-benzyl-3-deoxy-6-O-tosyl-D-mannose diethyl dithioacetal

Guidance literature:: DOI:10.1246/cl.1984.513

Reference yield:

: 17327-08-1
Methyl 3-acetamido-4,6-O-benzylidene-3-deoxy-α-D-glucopyranoside

: 90706-23-3
3-acetamido-2,4,5-tri-O-benzyl-3-deoxy-6-O-tosyl-D-mannose diethyl dithioacetal

Guidance literature:: Multi-step reaction with 9 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

7: 1.) sodium hydride / 1.) DMF, 20 min; 2.) DMF, overnight

8: toluene-p-sulfonic acid monohydrate / methanol / 2 h

9: 77 percent / pyridine / 16 h

With pyridine; hydrogenchloride; dmap; sodium methylate; sodium acetate; sodium hydride; toluene-4-sulfonic acid; In pyridine; methanol;
DOI:10.1016/0008-6215(85)85186-7

Reference yield:

: 90706-18-6
methyl 3-acetamido-4,6-O-benzylidene-3-deoxy-2-O-mesyl-α-D-glucopyranoside

: 90706-23-3
3-acetamido-2,4,5-tri-O-benzyl-3-deoxy-6-O-tosyl-D-mannose diethyl dithioacetal

Guidance literature:: Multi-step reaction with 8 steps

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

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

3: 1.) 2M HCl; 2.) pyridine / 1.) reflux, 13 h; 2.) overnight

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

5: 4-dimethylaminopyridine / pyridine / 3.5 h / 70 °C

6: 1.) sodium hydride / 1.) DMF, 20 min; 2.) DMF, overnight

7: toluene-p-sulfonic acid monohydrate / methanol / 2 h

8: 77 percent / pyridine / 16 h

With pyridine; hydrogenchloride; dmap; sodium methylate; sodium acetate; sodium hydride; toluene-4-sulfonic acid; In pyridine; methanol;
DOI:10.1016/0008-6215(85)85186-7