(2S)-(tert-butyldimethylsilanyloxymethyl)-1-(2,3,4,6-tetra-O-benzyl-β-D-galactopyranosyl)-pent-4-ene

Base Information

Chemical Name:(2S)-(tert-butyldimethylsilanyloxymethyl)-1-(2,3,4,6-tetra-O-benzyl-β-D-galactopyranosyl)-pent-4-ene
CAS No.:881015-89-0
Molecular Formula:C₄₆H₆₀O₆Si
Molecular Weight:737.064
Hs Code.:

Synonyms:(2S)-(tert-butyldimethylsilanyloxymethyl)-1-(2,3,4,6-tetra-O-benzyl-β-D-galactopyranosyl)-pent-4-ene

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Chemical Property of (2S)-(tert-butyldimethylsilanyloxymethyl)-1-(2,3,4,6-tetra-O-benzyl-β-D-galactopyranosyl)-pent-4-ene

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Technology Process of (2S)-(tert-butyldimethylsilanyloxymethyl)-1-(2,3,4,6-tetra-O-benzyl-β-D-galactopyranosyl)-pent-4-ene

There total 5 articles about (2S)-(tert-butyldimethylsilanyloxymethyl)-1-(2,3,4,6-tetra-O-benzyl-β-D-galactopyranosyl)-pent-4-ene 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:

: 881015-88-9
(S)-2-((2S,3S,4R,5S,6R)-3,4,5-Tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-ylmethyl)-pent-4-en-1-ol

: 69739-34-0
t-butyldimethylsiyl triflate

: 881015-89-0
(2S)-(tert-butyldimethylsilanyloxymethyl)-1-(2,3,4,6-tetra-O-benzyl-β-D-galactopyranosyl)-pent-4-ene

Guidance literature:: With 2,3,5-trimethyl-pyridine; In dichloromethane; at 20 ℃; for 0.333333h;
DOI:10.1021/jo052256z

Reference yield:

: C₄₂H₄₈O₈

: 881015-89-0
(2S)-(tert-butyldimethylsilanyloxymethyl)-1-(2,3,4,6-tetra-O-benzyl-β-D-galactopyranosyl)-pent-4-ene

Guidance literature:: Multi-step reaction with 4 steps

1: 13.1 g / Et₃N*HCl; BuLi / tetrahydrofuran; hexane / 0.5 h / -78 °C

2: 70 percent / NaHMDS / tetrahydrofuran / -78 - 20 °C

3: LiAlH₄ / diethyl ether / 0.25 h / 20 °C

4: 2.33 g / 2,3,5-collidine / CH₂Cl₂ / 0.33 h / 20 °C

With 2,3,5-trimethyl-pyridine; lithium aluminium tetrahydride; n-butyllithium; sodium hexamethyldisilazane; triethylamine hydrochloride; In tetrahydrofuran; diethyl ether; hexane; dichloromethane;
DOI:10.1021/jo052256z

Reference yield:

: 881015-86-7
(4S)-4-benzyl-3-[3-(2,3,4,6-tetra-O-benzyl-β-D-galactopyranosyl)propionyl]oxazolidin-2-one

: 881015-89-0
(2S)-(tert-butyldimethylsilanyloxymethyl)-1-(2,3,4,6-tetra-O-benzyl-β-D-galactopyranosyl)-pent-4-ene

Guidance literature:: Multi-step reaction with 3 steps

1: 70 percent / NaHMDS / tetrahydrofuran / -78 - 20 °C

2: LiAlH₄ / diethyl ether / 0.25 h / 20 °C

3: 2.33 g / 2,3,5-collidine / CH₂Cl₂ / 0.33 h / 20 °C

With 2,3,5-trimethyl-pyridine; lithium aluminium tetrahydride; sodium hexamethyldisilazane; In tetrahydrofuran; diethyl ether; dichloromethane;
DOI:10.1021/jo052256z