methyl N-[6,7-dideoxy-1,2:3,4-di-O-isopropylidene-7-[[(1'S)-1'-phenylethyl]amino]-L-glycero-α-D-galactooctopyranuronoyl]glycinate

Base Information

Chemical Name:methyl N-[6,7-dideoxy-1,2:3,4-di-O-isopropylidene-7-[[(1'S)-1'-phenylethyl]amino]-L-glycero-α-D-galactooctopyranuronoyl]glycinate
CAS No.:206127-76-6
Molecular Formula:C₂₅H₃₆N₂O₈
Molecular Weight:492.569
Hs Code.:

Synonyms:methyl N-[6,7-dideoxy-1,2:3,4-di-O-isopropylidene-7-[[(1'S)-1'-phenylethyl]amino]-L-glycero-α-D-galactooctopyranuronoyl]glycinate

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Chemical Property of methyl N-[6,7-dideoxy-1,2:3,4-di-O-isopropylidene-7-[[(1'S)-1'-phenylethyl]amino]-L-glycero-α-D-galactooctopyranuronoyl]glycinate

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Technology Process of methyl N-[6,7-dideoxy-1,2:3,4-di-O-isopropylidene-7-[[(1'S)-1'-phenylethyl]amino]-L-glycero-α-D-galactooctopyranuronoyl]glycinate

There total 10 articles about methyl N-[6,7-dideoxy-1,2:3,4-di-O-isopropylidene-7-[[(1'S)-1'-phenylethyl]amino]-L-glycero-α-D-galactooctopyranuronoyl]glycinate 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: 69.0%

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

: 206127-74-4
methyl 7-[[(1'S)-1'-phenylethyl]amino]-6,7-dideoxy-1,2:3,4-di-O-isopropylidene-L-glycero-α-D-galactooctopyranuronate

: 206127-76-6
methyl N-[6,7-dideoxy-1,2:3,4-di-O-isopropylidene-7-[[(1'S)-1'-phenylethyl]amino]-L-glycero-α-D-galactooctopyranuronoyl]glycinate

Guidance literature:: methyl 7-[[(1'S)-1'-phenylethyl]amino]-6,7-dideoxy-1,2:3,4-di-O-isopropylidene-L-glycero-α-D-galactooctopyranuronate; With potassium hydroxide; In tetrahydrofuran; methanol; for 4h; Heating;

glycine ethyl ester hydrochloride; With (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; triethylamine; In chloroform; at 20 ℃; for 4h;
DOI:10.1016/S0040-4020(01)00600-7

Reference yield:

: 120449-66-3
isopropyl 6-deoxy-7-oxo-1,2:3,4-di-O-isopropylidene-α-D-galacto-octopyranuronate

: 206127-76-6
methyl N-[6,7-dideoxy-1,2:3,4-di-O-isopropylidene-7-[[(1'S)-1'-phenylethyl]amino]-L-glycero-α-D-galactooctopyranuronoyl]glycinate

Guidance literature:: Multi-step reaction with 4 steps

1.1: benzene / 13 h / Heating

2.1: H₂ / Pd/C / benzene / 8 h / 20 °C / 7500.6 Torr

3.1: 83 percent / BuLi / tetrahydrofuran; hexane / 2.5 h / 60 °C

4.1: KOH / methanol; tetrahydrofuran / 4 h / Heating

4.2: 69 percent / Et₃N; BOP / CHCl₃ / 4 h / 20 °C

With potassium hydroxide; n-butyllithium; hydrogen; palladium on activated charcoal; In tetrahydrofuran; methanol; hexane; benzene;
DOI:10.1016/S0040-4020(01)00600-7

Reference yield:

: 2-[(E)-(S)-1-Phenyl-ethylimino]-3-((3aR,5R,5aS,8aS,8bR)-2,2,7,7-tetramethyl-tetrahydro-bis[1,3]dioxolo[4,5-b;4',5'-d]pyran-5-yl)-propionic acid isopropyl ester

: 206127-76-6
methyl N-[6,7-dideoxy-1,2:3,4-di-O-isopropylidene-7-[[(1'S)-1'-phenylethyl]amino]-L-glycero-α-D-galactooctopyranuronoyl]glycinate

Guidance literature:: Multi-step reaction with 3 steps

1.1: H₂ / Pd/C / benzene / 8 h / 20 °C / 7500.6 Torr

2.1: 83 percent / BuLi / tetrahydrofuran; hexane / 2.5 h / 60 °C

3.1: KOH / methanol; tetrahydrofuran / 4 h / Heating

3.2: 69 percent / Et₃N; BOP / CHCl₃ / 4 h / 20 °C

With potassium hydroxide; n-butyllithium; hydrogen; palladium on activated charcoal; In tetrahydrofuran; methanol; hexane; benzene;
DOI:10.1016/S0040-4020(01)00600-7