(2'S,3'S,4'R)-1-(2,3,4,6-tetra-O-benzyl-α-C-D-galactopyranosyl)-2-(3',4';-O-isopropylidene-D-ribo-heptadecyl)-ethane

Base Information

Chemical Name:(2'S,3'S,4'R)-1-(2,3,4,6-tetra-O-benzyl-α-C-D-galactopyranosyl)-2-(3',4';-O-isopropylidene-D-ribo-heptadecyl)-ethane
CAS No.:1221720-10-0
Molecular Formula:C₅₆H₇₈O₈
Molecular Weight:879.231
Hs Code.:

Synonyms:(2'S,3'S,4'R)-1-(2,3,4,6-tetra-O-benzyl-α-C-D-galactopyranosyl)-2-(3',4';-O-isopropylidene-D-ribo-heptadecyl)-ethane

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Chemical Property of (2'S,3'S,4'R)-1-(2,3,4,6-tetra-O-benzyl-α-C-D-galactopyranosyl)-2-(3',4';-O-isopropylidene-D-ribo-heptadecyl)-ethane

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Technology Process of (2'S,3'S,4'R)-1-(2,3,4,6-tetra-O-benzyl-α-C-D-galactopyranosyl)-2-(3',4';-O-isopropylidene-D-ribo-heptadecyl)-ethane

There total 11 articles about (2'S,3'S,4'R)-1-(2,3,4,6-tetra-O-benzyl-α-C-D-galactopyranosyl)-2-(3',4';-O-isopropylidene-D-ribo-heptadecyl)-ethane 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: 84.0%

: 1221720-08-6
(2'S,3'S,4'R)-1-(2,3,4,6-tetra-O-benzyl-α-C-D-galactopyranosyl)-2-(3',4';-O-isopropylidene-2'-O-(para-methoxybenzyl)-D-ribo-heptadecyl)-ethane

: 1221720-10-0
(2'S,3'S,4'R)-1-(2,3,4,6-tetra-O-benzyl-α-C-D-galactopyranosyl)-2-(3',4';-O-isopropylidene-D-ribo-heptadecyl)-ethane

Guidance literature:: With 2,3-dicyano-5,6-dichloro-p-benzoquinone; In dichloromethane; water; at 20 ℃; for 0.666667h;
DOI:10.1016/j.bmcl.2011.02.044

Reference yield:

: 1221720-07-5
(2'S,3'S,4'R)-1-(2,3,4,6-tetra-O-benzyl-α-C-D-galactopyranosyl)-2-(3',4'-O-isopropylidene-2'-O-(para-methoxybenzyl)-D-ribo-heptadec-5',6'-enyl)-acetylene

: 1221720-10-0
(2'S,3'S,4'R)-1-(2,3,4,6-tetra-O-benzyl-α-C-D-galactopyranosyl)-2-(3',4';-O-isopropylidene-D-ribo-heptadecyl)-ethane

Guidance literature:: Multi-step reaction with 2 steps

1: sodium acetate; toluene-4-sulfonic acid hydrazide / 1,2-dimethoxyethane; water / Reflux

2: 2,3-dicyano-5,6-dichloro-p-benzoquinone / dichloromethane; water / 0.67 h / 20 °C

With sodium acetate; toluene-4-sulfonic acid hydrazide; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In 1,2-dimethoxyethane; dichloromethane; water;
DOI:10.1016/j.bmcl.2011.02.044

Reference yield:

: 174591-00-5
2,3-O-isopropylidene-1-trimethylsilylacetylene-D-ribo-butan-1,4-diol

: 1221720-10-0
(2'S,3'S,4'R)-1-(2,3,4,6-tetra-O-benzyl-α-C-D-galactopyranosyl)-2-(3',4';-O-isopropylidene-D-ribo-heptadecyl)-ethane

Guidance literature:: Multi-step reaction with 9 steps

1.1: dmap; triethylamine / dichloromethane / 0 - 20 °C

2.1: 1H-imidazole; tetra-(n-butyl)ammonium iodide; sodium hydride / tetrahydrofuran; N,N-dimethyl-formamide / 0 - 20 °C

3.1: n-butyllithium / diethyl ether / -78 - 0 °C

3.2: 1 h / 0 °C

4.1: sodium hydride / N,N-dimethyl-formamide / 0 - 20 °C

5.1: ammonium fluoride / methanol / 3 h / Reflux

6.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / 1 h / -78 °C

6.2: 1.5 h / -78 - 20 °C

7.1: n-butyllithium / tetrahydrofuran / -40 - -5 °C

7.2: -5 - 20 °C

8.1: sodium acetate; toluene-4-sulfonic acid hydrazide / 1,2-dimethoxyethane; water / Reflux

9.1: 2,3-dicyano-5,6-dichloro-p-benzoquinone / dichloromethane; water / 0.67 h / 20 °C

With 1H-imidazole; dmap; ammonium fluoride; n-butyllithium; oxalyl dichloride; sodium acetate; tetra-(n-butyl)ammonium iodide; sodium hydride; dimethyl sulfoxide; triethylamine; toluene-4-sulfonic acid hydrazide; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In tetrahydrofuran; methanol; 1,2-dimethoxyethane; diethyl ether; dichloromethane; water; N,N-dimethyl-formamide; 6.2: Swern oxidation / 7.2: Wittig reaction;
DOI:10.1016/j.bmcl.2011.02.044