methyl 2,3,6-tri-O-acetyl-4-O-(5-azido-6-p-tolylsulfonyloxyhexyl)-α-D-glucopyranoside

Base Information

Chemical Name:methyl 2,3,6-tri-O-acetyl-4-O-(5-azido-6-p-tolylsulfonyloxyhexyl)-α-D-glucopyranoside
CAS No.:172949-86-9
Molecular Formula:C₂₆H₃₇N₃O₁₂S
Molecular Weight:615.659
Hs Code.:

Synonyms:methyl 2,3,6-tri-O-acetyl-4-O-(5-azido-6-p-tolylsulfonyloxyhexyl)-α-D-glucopyranoside

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Chemical Property of methyl 2,3,6-tri-O-acetyl-4-O-(5-azido-6-p-tolylsulfonyloxyhexyl)-α-D-glucopyranoside

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Technology Process of methyl 2,3,6-tri-O-acetyl-4-O-(5-azido-6-p-tolylsulfonyloxyhexyl)-α-D-glucopyranoside

There total 10 articles about methyl 2,3,6-tri-O-acetyl-4-O-(5-azido-6-p-tolylsulfonyloxyhexyl)-α-D-glucopyranoside 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: 67.0%

: 98-59-9
p-toluenesulfonyl chloride

: 172949-85-8
methyl 2,3,6-tri-O-acetyl-4-O-(5-azido-6-hydroxyhexyl)-α-D-glucopyranoside

: 172949-86-9
methyl 2,3,6-tri-O-acetyl-4-O-(5-azido-6-p-tolylsulfonyloxyhexyl)-α-D-glucopyranoside

Guidance literature:: With dmap; In dichloromethane;
DOI:10.1016/0008-6215(95)00089-C

Reference yield:

: 69380-65-0
1,2-O-isopropylidenehexane-1,2,6-triol 6-p-toluenesulphonate

: 172949-86-9
methyl 2,3,6-tri-O-acetyl-4-O-(5-azido-6-p-tolylsulfonyloxyhexyl)-α-D-glucopyranoside

Guidance literature:: Multi-step reaction with 10 steps

1: 70 percent / NaI / acetone / 5 h / Heating

2: 64 percent / NaH / dimethylformamide / 3 h / Ambient temperature

3: H₂ / 10percent Pd/C / methanol

4: pyridine

5: 75 percent / TFA / CHCl₃ / 12 h / Ambient temperature

6: 78.6 percent / pyridine / 10 h / Ambient temperature

7: 65 percent / 4-dimethylaminopyridine / CH₂Cl₂

8: 85 percent / NaN₃ / dimethylformamide / 8 h / 60 °C

9: 1.) ZnBr₂, 2.) methanol / 1.) CH₂Cl₂, 0.5 h, 2.) CH₂Cl₂, 20 min

10: 67 percent / 4-dimethylaminopyridine / CH₂Cl₂

With pyridine; methanol; dmap; sodium azide; hydrogen; sodium hydride; trifluoroacetic acid; sodium iodide; zinc dibromide; palladium on activated charcoal; In methanol; dichloromethane; chloroform; N,N-dimethyl-formamide; acetone;
DOI:10.1016/0008-6215(95)00089-C

Reference yield:

: 106681-40-7
6-iodo-1,2-O-isopropylidenehexane-1,2-diol

: 172949-86-9
methyl 2,3,6-tri-O-acetyl-4-O-(5-azido-6-p-tolylsulfonyloxyhexyl)-α-D-glucopyranoside

Guidance literature:: Multi-step reaction with 9 steps

1: 64 percent / NaH / dimethylformamide / 3 h / Ambient temperature

2: H₂ / 10percent Pd/C / methanol

3: pyridine

4: 75 percent / TFA / CHCl₃ / 12 h / Ambient temperature

5: 78.6 percent / pyridine / 10 h / Ambient temperature

6: 65 percent / 4-dimethylaminopyridine / CH₂Cl₂

7: 85 percent / NaN₃ / dimethylformamide / 8 h / 60 °C

8: 1.) ZnBr₂, 2.) methanol / 1.) CH₂Cl₂, 0.5 h, 2.) CH₂Cl₂, 20 min

9: 67 percent / 4-dimethylaminopyridine / CH₂Cl₂

With pyridine; methanol; dmap; sodium azide; hydrogen; sodium hydride; trifluoroacetic acid; zinc dibromide; palladium on activated charcoal; In methanol; dichloromethane; chloroform; N,N-dimethyl-formamide;
DOI:10.1016/0008-6215(95)00089-C