(3'S,4'R)-3'-amino-(E)-nonadec-5'-en-4'-olyl 2,3,4-tetra-O-benzyl-β-C-D-galactopyranoside

Base Information

Chemical Name:(3'S,4'R)-3'-amino-(E)-nonadec-5'-en-4'-olyl 2,3,4-tetra-O-benzyl-β-C-D-galactopyranoside
CAS No.:236388-66-2
Molecular Formula:C₅₃H₇₃NO₆
Molecular Weight:820.166
Hs Code.:

Synonyms:(3'S,4'R)-3'-amino-(E)-nonadec-5'-en-4'-olyl 2,3,4-tetra-O-benzyl-β-C-D-galactopyranoside

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Chemical Property of (3'S,4'R)-3'-amino-(E)-nonadec-5'-en-4'-olyl 2,3,4-tetra-O-benzyl-β-C-D-galactopyranoside

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Technology Process of (3'S,4'R)-3'-amino-(E)-nonadec-5'-en-4'-olyl 2,3,4-tetra-O-benzyl-β-C-D-galactopyranoside

There total 20 articles about (3'S,4'R)-3'-amino-(E)-nonadec-5'-en-4'-olyl 2,3,4-tetra-O-benzyl-β-C-D-galactopyranoside 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: 65.0%

: 236388-65-1
(3'S,4'R)-3'-aminononadec-5'-yn-4'-olyl 2,3,4-tetra-O-benzyl-β-C-D-galactopyranoside

: 236388-66-2
(3'S,4'R)-3'-amino-(E)-nonadec-5'-en-4'-olyl 2,3,4-tetra-O-benzyl-β-C-D-galactopyranoside

Guidance literature:: With lithium aluminium tetrahydride; In 1,2-dimethoxyethane; at 85 ℃; for 3h;
DOI:10.1021/jo990398l

Reference yield:

: 906545-88-8
(3S,4R,5E)-1-(2,3,4,6-tetra-O-benzyl-β-D-galactopyranosyl)-3-(tert-butoxycarbonylamino)-4-hydroxy-5-nonadecene

: 236388-66-2
(3'S,4'R)-3'-amino-(E)-nonadec-5'-en-4'-olyl 2,3,4-tetra-O-benzyl-β-C-D-galactopyranoside

Guidance literature:: With hydrogenchloride; In 1,4-dioxane; at 70 ℃; for 4h;
DOI:10.1021/ol061100y

Reference yield:

: 906545-77-5
(2,3,4,6-tetra-O-benzyl-1-C-vinyl-α-D-galactopyranosyloxy)-ethanoic acid

: 236388-66-2
(3'S,4'R)-3'-amino-(E)-nonadec-5'-en-4'-olyl 2,3,4-tetra-O-benzyl-β-C-D-galactopyranoside

Guidance literature:: Multi-step reaction with 11 steps

1.1: lithium diisopropylamide / tetrahydrofuran; heptane; ethylbenzene / 1 h / -78 °C

2.1: 1.60 g / diethyl ether / 0 °C

3.1: 91 percent / hydrogen / Pt/C / methanol / 5 h / 20 °C

4.1: 90 percent / triphenylphosphine; DMAP; diethyl azodicarboxylate / tetrahydrofuran / 2 h / 70 °C

5.1: 90 percent / sodium azide / dimethylformamide / 1 h / 85 °C

6.1: hydrogen sulfide; pyridine / H₂O / 18 h / 20 °C

7.1: 1.05 g / pyridine / CH₂Cl₂ / 4 h / 20 °C

8.1: n-BuLi / tetrahydrofuran; hexane / 0.33 h / -78 °C

8.2: 80 percent / tetrahydrofuran; hexane / -78 - 20 °C

9.1: 71 percent / potassium carbonate / tetrahydrofuran; acetonitrile / 18 h / 20 °C

10.1: L-Selectride

11.1: aq. HCl / dioxane / 4 h / 70 °C

With pyridine; hydrogenchloride; dmap; n-butyllithium; sodium azide; hydrogen sulfide; hydrogen; L-Selectride; potassium carbonate; triphenylphosphine; lithium diisopropyl amide; diethylazodicarboxylate; platinum on activated charcoal; In tetrahydrofuran; 1,4-dioxane; methanol; diethyl ether; hexane; n-heptane; dichloromethane; ethylbenzene; water; N,N-dimethyl-formamide; acetonitrile; 1.1: <2,3>-Wittig sigmatropic rearrangement / 4.1: Mitsunobu reaction / 9.1: Horner-Wadsworth-Emmons olefination;
DOI:10.1021/ol061100y