methyl (benzyl 4-O-acetyl-5-azido-3,5-dideoxy-9-O-(4-methoxybenzyl)-D-glycero-α-D-galacto-non-2-ulopyranosid)onate

Base Information

Chemical Name:methyl (benzyl 4-O-acetyl-5-azido-3,5-dideoxy-9-O-(4-methoxybenzyl)-D-glycero-α-D-galacto-non-2-ulopyranosid)onate
CAS No.:352437-57-1
Molecular Formula:C₂₇H₃₃N₃O₁₀
Molecular Weight:559.573
Hs Code.:

Synonyms:methyl (benzyl 4-O-acetyl-5-azido-3,5-dideoxy-9-O-(4-methoxybenzyl)-D-glycero-α-D-galacto-non-2-ulopyranosid)onate

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Chemical Property of methyl (benzyl 4-O-acetyl-5-azido-3,5-dideoxy-9-O-(4-methoxybenzyl)-D-glycero-α-D-galacto-non-2-ulopyranosid)onate

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Technology Process of methyl (benzyl 4-O-acetyl-5-azido-3,5-dideoxy-9-O-(4-methoxybenzyl)-D-glycero-α-D-galacto-non-2-ulopyranosid)onate

There total 11 articles about methyl (benzyl 4-O-acetyl-5-azido-3,5-dideoxy-9-O-(4-methoxybenzyl)-D-glycero-α-D-galacto-non-2-ulopyranosid)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: 60.0%

: 89238-99-3
O-(4-methoxybenzyl)-trichloroacetimidate

: 352437-56-0
methyl (benzyl 4-O-acetyl-5-azido-3,5-dideoxy-D-glycero-α-D-galacto-non-2-ulopyranosid)onate

: 352437-57-1
methyl (benzyl 4-O-acetyl-5-azido-3,5-dideoxy-9-O-(4-methoxybenzyl)-D-glycero-α-D-galacto-non-2-ulopyranosid)onate

Guidance literature:: With trimethylsilyl trifluoromethanesulfonate; In acetonitrile; at -23 ℃; for 0.5h;

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

: 352437-57-1
methyl (benzyl 4-O-acetyl-5-azido-3,5-dideoxy-9-O-(4-methoxybenzyl)-D-glycero-α-D-galacto-non-2-ulopyranosid)onate

Guidance literature:: Multi-step reaction with 9 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

7: 78 percent / pyridine / CH₂Cl₂ / 0 °C

8: 89 percent / EtSH; p-TsOH / CH₂Cl₂ / 4 h / 0 - 20 °C

9: 60 percent / TMSOTf / acetonitrile / 0.5 h / -23 °C

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

Reference yield:

: 101554-19-2
benzyl 5-amino-3,4-dideoxy-D-glycero-α-D-galacto-non-2-ulopyranosidonic acid

: 352437-57-1
methyl (benzyl 4-O-acetyl-5-azido-3,5-dideoxy-9-O-(4-methoxybenzyl)-D-glycero-α-D-galacto-non-2-ulopyranosid)onate

Guidance literature:: Multi-step reaction with 8 steps

1: 70 percent / TfN₃; NaOMe; DMAP / methanol / 20 °C

2: pyridine

3: 2.324 g / CH₂Cl₂; diethyl ether

4: 97 percent / NaOMe / methanol

5: 85 percent / p-TsOH*H₂O / acetone / 17 h

6: 78 percent / pyridine / CH₂Cl₂ / 0 °C

7: 89 percent / EtSH; p-TsOH / CH₂Cl₂ / 4 h / 0 - 20 °C

8: 60 percent / TMSOTf / acetonitrile / 0.5 h / -23 °C

With pyridine; dmap; trimethylsilyl trifluoromethanesulfonate; triflic azide; sodium methylate; toluene-4-sulfonic acid; ethanethiol; In methanol; diethyl ether; dichloromethane; acetone; acetonitrile; 4: Zemplen deacetylation;