(2'S,3'S,4'S)-1-(2,3,4,6-tetra-O-benzyl-α-C-D-galactopyranosyl)-2-(3',4'-O-isopropylidene-5'-O-(tert-butyldimethylsilyl)-2'-O-(para-methoxybenzyl)-D-ribo-butyl)-acetylene

Base Information

Chemical Name:(2'S,3'S,4'S)-1-(2,3,4,6-tetra-O-benzyl-α-C-D-galactopyranosyl)-2-(3',4'-O-isopropylidene-5'-O-(tert-butyldimethylsilyl)-2'-O-(para-methoxybenzyl)-D-ribo-butyl)-acetylene
CAS No.:1221720-05-3
Molecular Formula:C₅₇H₇₀O₁₀Si
Molecular Weight:943.262
Hs Code.:

(2'S,3'S,4'S)-1-(2,3,4,6-tetra-O-benzyl-α-C-D-galactopyranosyl)-2-(3',4'-O-isopropylidene-5'-O-(tert-butyldimethylsilyl)-2'-O-(para-methoxybenzyl)-D-ribo-butyl)-acetylene

Synonyms:(2'S,3'S,4'S)-1-(2,3,4,6-tetra-O-benzyl-α-C-D-galactopyranosyl)-2-(3',4'-O-isopropylidene-5'-O-(tert-butyldimethylsilyl)-2'-O-(para-methoxybenzyl)-D-ribo-butyl)-acetylene

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Chemical Property of (2'S,3'S,4'S)-1-(2,3,4,6-tetra-O-benzyl-α-C-D-galactopyranosyl)-2-(3',4'-O-isopropylidene-5'-O-(tert-butyldimethylsilyl)-2'-O-(para-methoxybenzyl)-D-ribo-butyl)-acetylene

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Technology Process of (2'S,3'S,4'S)-1-(2,3,4,6-tetra-O-benzyl-α-C-D-galactopyranosyl)-2-(3',4'-O-isopropylidene-5'-O-(tert-butyldimethylsilyl)-2'-O-(para-methoxybenzyl)-D-ribo-butyl)-acetylene

There total 6 articles about (2'S,3'S,4'S)-1-(2,3,4,6-tetra-O-benzyl-α-C-D-galactopyranosyl)-2-(3',4'-O-isopropylidene-5'-O-(tert-butyldimethylsilyl)-2'-O-(para-methoxybenzyl)-D-ribo-butyl)-acetylene 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: 86.0%

: 1221720-04-2
(2'S,3'S,4'S)-1-(2,3,4-tri-O-benzyl-α-C-D-galactopyranosyl)-2-(3',4'-O-isopropylidene-5'-O-(tert-butyldimethylsilyl)-2'-O-(para-methoxybenzyl)-D-ribo-butyl)-acetylene

: 100-39-0
benzyl bromide

: 1221720-05-3
(2'S,3'S,4'S)-1-(2,3,4,6-tetra-O-benzyl-α-C-D-galactopyranosyl)-2-(3',4'-O-isopropylidene-5'-O-(tert-butyldimethylsilyl)-2'-O-(para-methoxybenzyl)-D-ribo-butyl)-acetylene

Guidance literature:: With sodium hydride; In N,N-dimethyl-formamide; at 0 - 20 ℃;
DOI:10.1016/j.bmcl.2011.02.044

Reference yield:

: 1221720-02-0
1-(2,3-O-isopropylidene-4-O-(tert-butyldimethylsilyl)-1-trimethylsilylacetylene)-D-ribo-butan-1-ol

: 1221720-05-3
(2'S,3'S,4'S)-1-(2,3,4,6-tetra-O-benzyl-α-C-D-galactopyranosyl)-2-(3',4'-O-isopropylidene-5'-O-(tert-butyldimethylsilyl)-2'-O-(para-methoxybenzyl)-D-ribo-butyl)-acetylene

Guidance literature:: Multi-step reaction with 3 steps

1.1: 1H-imidazole; tetra-(n-butyl)ammonium iodide; sodium hydride / tetrahydrofuran; N,N-dimethyl-formamide / 0 - 20 °C

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

2.2: 1 h / 0 °C

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

With 1H-imidazole; n-butyllithium; tetra-(n-butyl)ammonium iodide; sodium hydride; In tetrahydrofuran; diethyl ether; N,N-dimethyl-formamide;
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

: 1221720-05-3
(2'S,3'S,4'S)-1-(2,3,4,6-tetra-O-benzyl-α-C-D-galactopyranosyl)-2-(3',4'-O-isopropylidene-5'-O-(tert-butyldimethylsilyl)-2'-O-(para-methoxybenzyl)-D-ribo-butyl)-acetylene

Guidance literature:: Multi-step reaction with 4 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

With 1H-imidazole; dmap; n-butyllithium; tetra-(n-butyl)ammonium iodide; sodium hydride; triethylamine; In tetrahydrofuran; diethyl ether; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1016/j.bmcl.2011.02.044