methyl 2-[(1R,2R,3S,4S,5R,6R)-2-(benzyloxycarbonylamino)-5,6-bis(tert-butyldimethylsilyloxy)-3,4-(isopropylidendioxy)cyclohexanecarboxamido]acetate

Base Information

Chemical Name:methyl 2-[(1R,2R,3S,4S,5R,6R)-2-(benzyloxycarbonylamino)-5,6-bis(tert-butyldimethylsilyloxy)-3,4-(isopropylidendioxy)cyclohexanecarboxamido]acetate
CAS No.:1380312-72-0
Molecular Formula:C₃₃H₅₆N₂O₉Si₂
Molecular Weight:680.987
Hs Code.:

methyl 2-[(1R,2R,3S,4S,5R,6R)-2-(benzyloxycarbonylamino)-5,6-bis(tert-butyldimethylsilyloxy)-3,4-(isopropylidendioxy)cyclohexanecarboxamido]acetate

Synonyms:methyl 2-[(1R,2R,3S,4S,5R,6R)-2-(benzyloxycarbonylamino)-5,6-bis(tert-butyldimethylsilyloxy)-3,4-(isopropylidendioxy)cyclohexanecarboxamido]acetate

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Chemical Property of methyl 2-[(1R,2R,3S,4S,5R,6R)-2-(benzyloxycarbonylamino)-5,6-bis(tert-butyldimethylsilyloxy)-3,4-(isopropylidendioxy)cyclohexanecarboxamido]acetate

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Technology Process of methyl 2-[(1R,2R,3S,4S,5R,6R)-2-(benzyloxycarbonylamino)-5,6-bis(tert-butyldimethylsilyloxy)-3,4-(isopropylidendioxy)cyclohexanecarboxamido]acetate

There total 7 articles about methyl 2-[(1R,2R,3S,4S,5R,6R)-2-(benzyloxycarbonylamino)-5,6-bis(tert-butyldimethylsilyloxy)-3,4-(isopropylidendioxy)cyclohexanecarboxamido]acetate 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: 83.0%

: 1380312-71-9
(1R,2R,3S,4S,5R,6R)-2-(benzyloxycarbonylamino)-5,6-bis(tertbutyldimethylsilyloxy)-3,4-(isopropylidenedioxy)cyclohexanecarboxylic acid

: 5680-79-5,883886-67-7
glycine ethyl ester hydrochloride

: 1380312-72-0
methyl 2-[(1R,2R,3S,4S,5R,6R)-2-(benzyloxycarbonylamino)-5,6-bis(tert-butyldimethylsilyloxy)-3,4-(isopropylidendioxy)cyclohexanecarboxamido]acetate

Guidance literature:: (1R,2R,3S,4S,5R,6R)-2-(benzyloxycarbonylamino)-5,6-bis(tertbutyldimethylsilyloxy)-3,4-(isopropylidenedioxy)cyclohexanecarboxylic acid; glycine ethyl ester hydrochloride; With O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; In N,N-dimethyl-formamide; at 20 ℃; for 0.333333h; Inert atmosphere;

With N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide; at 20 ℃; for 12h; Inert atmosphere;
DOI:10.1002/ejoc.201200103

Reference yield:

: 1380312-70-8
methyl (1R,2R,3S,4R,5S,6R)-2-(benzyloxycarbonylamino)-5,6-dihydroxy-3,4-(isopropylidenedioxy)cyclohexanecarboxylate

: 1380312-72-0
methyl 2-[(1R,2R,3S,4S,5R,6R)-2-(benzyloxycarbonylamino)-5,6-bis(tert-butyldimethylsilyloxy)-3,4-(isopropylidendioxy)cyclohexanecarboxamido]acetate

Guidance literature:: Multi-step reaction with 3 steps

1.1: barium hydroxide octahydrate / tetrahydrofuran; water / 1 h / 20 °C / Inert atmosphere

2.1: 1H-imidazole / methanol; N,N-dimethyl-formamide / 17 h / 80 °C / Inert atmosphere

3.1: O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate / N,N-dimethyl-formamide / 0.33 h / 20 °C / Inert atmosphere

3.2: 12 h / 20 °C / Inert atmosphere

With 1H-imidazole; barium hydroxide octahydrate; O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; In tetrahydrofuran; methanol; water; N,N-dimethyl-formamide;
DOI:10.1002/ejoc.201200103

Reference yield:

: 1380312-69-5
methyl (1R,2R,3S,4S,5S,6R)-3-(benzyloxy)-2-hydroxy-4,5-(isopropylidenedioxy)-6-nitrocyclohexanecarboxylate

: 1380312-72-0
methyl 2-[(1R,2R,3S,4S,5R,6R)-2-(benzyloxycarbonylamino)-5,6-bis(tert-butyldimethylsilyloxy)-3,4-(isopropylidendioxy)cyclohexanecarboxamido]acetate

Guidance literature:: Multi-step reaction with 5 steps

1.1: palladium 10% on activated carbon; hydrogen; citric acid / methanol / 48 h / 20 °C / 760.05 Torr

2.1: sodium hydrogencarbonate / methanol; water / 3 h / 0 - 20 °C / Inert atmosphere

3.1: barium hydroxide octahydrate / tetrahydrofuran; water / 1 h / 20 °C / Inert atmosphere

4.1: 1H-imidazole / methanol; N,N-dimethyl-formamide / 17 h / 80 °C / Inert atmosphere

5.1: O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate / N,N-dimethyl-formamide / 0.33 h / 20 °C / Inert atmosphere

5.2: 12 h / 20 °C / Inert atmosphere

With 1H-imidazole; barium hydroxide octahydrate; palladium 10% on activated carbon; hydrogen; sodium hydrogencarbonate; O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; citric acid; In tetrahydrofuran; methanol; water; N,N-dimethyl-formamide;
DOI:10.1002/ejoc.201200103