2,3-di-O-benzyl-N-benzyloxycarbonyl-1,5-dideoxy-1,5-imino-4,6-O-isopropylidene-D-glucitol

Base Information

Chemical Name:2,3-di-O-benzyl-N-benzyloxycarbonyl-1,5-dideoxy-1,5-imino-4,6-O-isopropylidene-D-glucitol
CAS No.:130539-13-8
Molecular Formula:C₃₁H₃₅NO₆
Molecular Weight:517.622
Hs Code.:

Synonyms:2,3-di-O-benzyl-N-benzyloxycarbonyl-1,5-dideoxy-1,5-imino-4,6-O-isopropylidene-D-glucitol

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Chemical Property of 2,3-di-O-benzyl-N-benzyloxycarbonyl-1,5-dideoxy-1,5-imino-4,6-O-isopropylidene-D-glucitol

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Technology Process of 2,3-di-O-benzyl-N-benzyloxycarbonyl-1,5-dideoxy-1,5-imino-4,6-O-isopropylidene-D-glucitol

There total 5 articles about 2,3-di-O-benzyl-N-benzyloxycarbonyl-1,5-dideoxy-1,5-imino-4,6-O-isopropylidene-D-glucitol 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: 81.0%

: 100-39-0
benzyl bromide

: 130609-18-6
N-benzyloxycarbonyl-1,5-dideoxy-1,5-imino-4,6-O-isopropylidene-D-glucitol

: 130539-13-8
2,3-di-O-benzyl-N-benzyloxycarbonyl-1,5-dideoxy-1,5-imino-4,6-O-isopropylidene-D-glucitol

Guidance literature:: With sodium hydride; In N,N-dimethyl-formamide; at 0 - 20 ℃; for 6h;
DOI:10.17344/acsi.2018.4255

Reference yield: 70.0%

: 100-39-0
benzyl bromide

: 130609-18-6
N-benzyloxycarbonyl-1,5-dideoxy-1,5-imino-4,6-O-isopropylidene-D-glucitol

: N-benzyloxycarbonyl-2-O-benzyl-1,5-dideoxy-1,5-imino-4,6-O-isopropylidene-D-glucitol

: N-benzyloxycarbonyl-3-O-benzyl-1,5-dideoxy-1,5-imino-4,6-O-isopropylidene-D-glucitol

: 130539-13-8
2,3-di-O-benzyl-N-benzyloxycarbonyl-1,5-dideoxy-1,5-imino-4,6-O-isopropylidene-D-glucitol

Guidance literature:: With tetrabutylammomium bromide; sodium hydroxide; In dichloromethane; at 25 ℃; for 24h; regioselective reaction;
DOI:10.17344/acsi.2018.4255

Reference yield:

: 19130-96-2
1,5-dideoxy-1,5-imino-D-glucitol

: 130539-13-8
2,3-di-O-benzyl-N-benzyloxycarbonyl-1,5-dideoxy-1,5-imino-4,6-O-isopropylidene-D-glucitol

Guidance literature:: Multi-step reaction with 2 steps

1: 1) NaHCO₃, 2) TsOH / 1) DMF, 90 min, 2) pH 2.5, 90 min, 40 deg C

2: 1) NaH / 1) DMF, <10 deg C, 2) r.t., 16 h

With sodium hydride; sodium hydrogencarbonate; toluene-4-sulfonic acid;
DOI:10.1016/0008-6215(90)80031-W