methyl (benzyl 5-azido-7,8-O-isopropylidene-3,5-di-deoxy-D-glycero-α-D-galacto-non-2-ulopyranoside)onate

Base Information

Chemical Name:methyl (benzyl 5-azido-7,8-O-isopropylidene-3,5-di-deoxy-D-glycero-α-D-galacto-non-2-ulopyranoside)onate
CAS No.:352437-53-7
Molecular Formula:C₂₀H₂₇N₃O₈
Molecular Weight:437.45
Hs Code.:

Synonyms:methyl (benzyl 5-azido-7,8-O-isopropylidene-3,5-di-deoxy-D-glycero-α-D-galacto-non-2-ulopyranoside)onate

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Chemical Property of methyl (benzyl 5-azido-7,8-O-isopropylidene-3,5-di-deoxy-D-glycero-α-D-galacto-non-2-ulopyranoside)onate

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Technology Process of methyl (benzyl 5-azido-7,8-O-isopropylidene-3,5-di-deoxy-D-glycero-α-D-galacto-non-2-ulopyranoside)onate

There total 14 articles about methyl (benzyl 5-azido-7,8-O-isopropylidene-3,5-di-deoxy-D-glycero-α-D-galacto-non-2-ulopyranoside)onate 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: 90.0%

: 77-76-9
2,2-dimethoxy-propane

: 352437-49-1
methyl (benzyl 5-azido-4,7,8,9-tetra-O-acetyl-3,5-di-deoxy-D-glycero-α-D-galacto-non-2-ulopyranoside)onate

: 352437-53-7
methyl (benzyl 5-azido-7,8-O-isopropylidene-3,5-di-deoxy-D-glycero-α-D-galacto-non-2-ulopyranoside)onate

Guidance literature:: methyl (benzyl 5-azido-4,7,8,9-tetra-O-acetyl-3,5-di-deoxy-D-glycero-α-D-galacto-non-2-ulopyranoside)onate; With sodium methylate; In methanol; at 20 ℃; for 1h;

2,2-dimethoxy-propane; With camphor-10-sulfonic acid; at 20 ℃; for 3h; Inert atmosphere;
DOI:10.1002/anie.201909177

Reference yield: 85.0%

: 77-76-9
2,2-dimethoxy-propane

: 352437-51-5
methyl (benzyl 5-azido-3,5-dideoxy-D-glycero-α-D-galacto-non-2-ulopyranosid)onate

: 352437-53-7
methyl (benzyl 5-azido-7,8-O-isopropylidene-3,5-di-deoxy-D-glycero-α-D-galacto-non-2-ulopyranoside)onate

Guidance literature:: With toluene-4-sulfonic acid; In acetone; for 17h;

Reference yield:

: 19342-75-7
methyl (benzyl 5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-α-D-glycero-D-galacto-2-nonulopyranosid)onate

: 352437-53-7
methyl (benzyl 5-azido-7,8-O-isopropylidene-3,5-di-deoxy-D-glycero-α-D-galacto-non-2-ulopyranoside)onate

Guidance literature:: Multi-step reaction with 6 steps

1: KOH / butan-1-ol

2: 70 percent / TfN₃; NaOMe; DMAP / methanol / 20 °C

3: pyridine

4: 2.324 g / CH₂Cl₂; diethyl ether

5: 97 percent / NaOMe / methanol

6: 85 percent / p-TsOH*H₂O / acetone / 17 h

With pyridine; dmap; potassium hydroxide; triflic azide; sodium methylate; toluene-4-sulfonic acid; In methanol; diethyl ether; dichloromethane; acetone; butan-1-ol; 5: Zemplen deacetylation;