(3R)-3-(tert-butyldimethylsilanyloxymethyl)-4-(2,3,4,6-tetra-O-benzyl-β-D-galactopyranosyl)butyraldehyde

Base Information

Chemical Name:(3R)-3-(tert-butyldimethylsilanyloxymethyl)-4-(2,3,4,6-tetra-O-benzyl-β-D-galactopyranosyl)butyraldehyde
CAS No.:881015-90-3
Molecular Formula:C₄₅H₅₈O₇Si
Molecular Weight:739.037
Hs Code.:

Synonyms:(3R)-3-(tert-butyldimethylsilanyloxymethyl)-4-(2,3,4,6-tetra-O-benzyl-β-D-galactopyranosyl)butyraldehyde

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Chemical Property of (3R)-3-(tert-butyldimethylsilanyloxymethyl)-4-(2,3,4,6-tetra-O-benzyl-β-D-galactopyranosyl)butyraldehyde

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Technology Process of (3R)-3-(tert-butyldimethylsilanyloxymethyl)-4-(2,3,4,6-tetra-O-benzyl-β-D-galactopyranosyl)butyraldehyde

There total 7 articles about (3R)-3-(tert-butyldimethylsilanyloxymethyl)-4-(2,3,4,6-tetra-O-benzyl-β-D-galactopyranosyl)butyraldehyde 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: 96.0%

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

: 881015-90-3
(3R)-3-(tert-butyldimethylsilanyloxymethyl)-4-(2,3,4,6-tetra-O-benzyl-β-D-galactopyranosyl)butyraldehyde

Guidance literature:: (2S)-(tert-butyldimethylsilanyloxymethyl)-1-(2,3,4,6-tetra-O-benzyl-β-D-galactopyranosyl)-pent-4-ene; With ozone; In dichloromethane; at -78 ℃;

With PS-PPh₃; In dichloromethane; at -78 - 20 ℃; for 14h;
DOI:10.1021/jo052256z

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

: 881015-90-3
(3R)-3-(tert-butyldimethylsilanyloxymethyl)-4-(2,3,4,6-tetra-O-benzyl-β-D-galactopyranosyl)butyraldehyde

Guidance literature:: Multi-step reaction with 2 steps

1.1: 2.33 g / 2,3,5-collidine / CH₂Cl₂ / 0.33 h / 20 °C

2.1: O₃ / CH₂Cl₂ / -78 °C

2.2: 96 percent / PS-PPh₃ / CH₂Cl₂ / 14 h / -78 - 20 °C

With 2,3,5-trimethyl-pyridine; ozone; In dichloromethane;
DOI:10.1021/jo052256z

Reference yield:

: C₄₂H₄₈O₈

: 881015-90-3
(3R)-3-(tert-butyldimethylsilanyloxymethyl)-4-(2,3,4,6-tetra-O-benzyl-β-D-galactopyranosyl)butyraldehyde

Guidance literature:: Multi-step reaction with 5 steps

1.1: 13.1 g / Et₃N*HCl; BuLi / tetrahydrofuran; hexane / 0.5 h / -78 °C

2.1: 70 percent / NaHMDS / tetrahydrofuran / -78 - 20 °C

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

4.1: 2.33 g / 2,3,5-collidine / CH₂Cl₂ / 0.33 h / 20 °C

5.1: O₃ / CH₂Cl₂ / -78 °C

5.2: 96 percent / PS-PPh₃ / CH₂Cl₂ / 14 h / -78 - 20 °C

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