ethyl N-benzyloxycarbonyl-4,7-dideoxy-4,7-imino-5,6-O-isopropylidene-L-glycero-L-gluco-heptanonate

Base Information

Chemical Name:ethyl N-benzyloxycarbonyl-4,7-dideoxy-4,7-imino-5,6-O-isopropylidene-L-glycero-L-gluco-heptanonate
CAS No.:674810-60-7
Molecular Formula:C₂₀H₂₇NO₈
Molecular Weight:409.436
Hs Code.:

Synonyms:ethyl N-benzyloxycarbonyl-4,7-dideoxy-4,7-imino-5,6-O-isopropylidene-L-glycero-L-gluco-heptanonate

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Chemical Property of ethyl N-benzyloxycarbonyl-4,7-dideoxy-4,7-imino-5,6-O-isopropylidene-L-glycero-L-gluco-heptanonate

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Technology Process of ethyl N-benzyloxycarbonyl-4,7-dideoxy-4,7-imino-5,6-O-isopropylidene-L-glycero-L-gluco-heptanonate

There total 6 articles about ethyl N-benzyloxycarbonyl-4,7-dideoxy-4,7-imino-5,6-O-isopropylidene-L-glycero-L-gluco-heptanonate 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: 61.0%

: 674810-55-0
ethyl (E)-N-benzyloxycarbonyl-2,3,4,7-tetradeoxy-4,7-imino-5,6-O-isopropylidene-L-ribo-hept-2-enonate

: 674810-59-4
ethyl N-benzyloxycarbonyl-4,7-dideoxy-4,7-imino-5,6-O-isopropylidene-L-glycero-L-altro-heptanonate

: 674810-60-7
ethyl N-benzyloxycarbonyl-4,7-dideoxy-4,7-imino-5,6-O-isopropylidene-L-glycero-L-gluco-heptanonate

Guidance literature:: With AD-mix-α; methanesulfonamide; In water; tert-butyl alcohol; at 25 ℃; for 16h;
DOI:10.1016/j.tetasy.2003.11.022

Reference yield:

: 117859-46-8
1,4-Dideoxy-2,3:5,6-di-O-isopropylidene-1,4-imino-D-allitol

: 674810-60-7
ethyl N-benzyloxycarbonyl-4,7-dideoxy-4,7-imino-5,6-O-isopropylidene-L-glycero-L-gluco-heptanonate

Guidance literature:: Multi-step reaction with 5 steps

1: 99 percent / NaHCO₃ / ethanol; H₂O / 2 h / 20 °C

2: 37 percent / H₂O; PTSA / methanol / 16 h / 20 °C

3: NaIO₄ / H₂O; tetrahydrofuran / 1.5 h / 0 °C

4: 88 percent / CH₂Cl₂ / 2 h / Heating

5: 61 percent / AD-mixβ; MeSO2NH2 / 2-methyl-propan-2-ol; H2O / 20 h / 25 °C

With sodium periodate; methanesulfonamide; water; sodium hydrogencarbonate; toluene-4-sulfonic acid; 1,4-bis(9-O-dihydroquinidine)phthalazine; In tetrahydrofuran; methanol; ethanol; dichloromethane; water; tert-butyl alcohol; 4: Wittig reaction / 5: Sharpless asymmetric dihydroxylation;
DOI:10.1016/j.tetasy.2003.11.022

Reference yield:

: 501-53-1,94274-21-2
benzyl chloroformate

: 674810-60-7
ethyl N-benzyloxycarbonyl-4,7-dideoxy-4,7-imino-5,6-O-isopropylidene-L-glycero-L-gluco-heptanonate

Guidance literature:: Multi-step reaction with 5 steps

1: 99 percent / NaHCO₃ / ethanol; H₂O / 2 h / 20 °C

2: 37 percent / H₂O; PTSA / methanol / 16 h / 20 °C

3: NaIO₄ / H₂O; tetrahydrofuran / 1.5 h / 0 °C

4: 88 percent / CH₂Cl₂ / 2 h / Heating

5: 61 percent / AD-mixβ; MeSO2NH2 / 2-methyl-propan-2-ol; H2O / 20 h / 25 °C

With sodium periodate; methanesulfonamide; water; sodium hydrogencarbonate; toluene-4-sulfonic acid; 1,4-bis(9-O-dihydroquinidine)phthalazine; In tetrahydrofuran; methanol; ethanol; dichloromethane; water; tert-butyl alcohol; 4: Wittig reaction / 5: Sharpless asymmetric dihydroxylation;
DOI:10.1016/j.tetasy.2003.11.022