(2S,3R,4R,5S)-1-Allyl-3,4,5-tris-benzyloxy-2-(tert-butyl-diphenyl-silanyloxymethyl)-piperidine

Base Information

Chemical Name:(2S,3R,4R,5S)-1-Allyl-3,4,5-tris-benzyloxy-2-(tert-butyl-diphenyl-silanyloxymethyl)-piperidine
CAS No.:441310-84-5
Molecular Formula:C₄₆H₅₃NO₄Si
Molecular Weight:712.017
Hs Code.:

Synonyms:(2S,3R,4R,5S)-1-Allyl-3,4,5-tris-benzyloxy-2-(tert-butyl-diphenyl-silanyloxymethyl)-piperidine

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Chemical Property of (2S,3R,4R,5S)-1-Allyl-3,4,5-tris-benzyloxy-2-(tert-butyl-diphenyl-silanyloxymethyl)-piperidine

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Technology Process of (2S,3R,4R,5S)-1-Allyl-3,4,5-tris-benzyloxy-2-(tert-butyl-diphenyl-silanyloxymethyl)-piperidine

There total 9 articles about (2S,3R,4R,5S)-1-Allyl-3,4,5-tris-benzyloxy-2-(tert-butyl-diphenyl-silanyloxymethyl)-piperidine 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: 73.0%

: 107-11-9,30551-89-4
1-amino-2-propene

: 441310-83-4
Methanesulfonic acid (1R,2S,3R,4S)-2,3,4-tris-benzyloxy-1-(tert-butyl-diphenyl-silanyloxymethyl)-5-methanesulfonyloxy-pentyl ester

: 441310-84-5
(2S,3R,4R,5S)-1-Allyl-3,4,5-tris-benzyloxy-2-(tert-butyl-diphenyl-silanyloxymethyl)-piperidine

Guidance literature:: at 70 ℃; for 39h;
DOI:10.1016/S0040-4039(02)00250-2

Reference yield:

: 100-39-0
benzyl bromide

: 441310-84-5
(2S,3R,4R,5S)-1-Allyl-3,4,5-tris-benzyloxy-2-(tert-butyl-diphenyl-silanyloxymethyl)-piperidine

Guidance literature:: Multi-step reaction with 5 steps

1: 85 percent / NaH; 18-crown-6 / tetrahydrofuran / 19 h / 70 °C

2: 70 percent / NBS / acetonitrile; H₂O / 2 h

3: 92 percent / NaBH₄ / ethanol / 20 h

4: 80 percent / Et₃N; DMAP / CH₂Cl₂ / 3 h / -15 °C

5: 73 percent / 39 h / 70 °C

With dmap; sodium tetrahydroborate; N-Bromosuccinimide; 18-crown-6 ether; sodium hydride; triethylamine; In tetrahydrofuran; ethanol; dichloromethane; water; acetonitrile;
DOI:10.1016/S0040-4039(02)00250-2

Reference yield:

: 182074-52-8
pent-4-enyl α,β-D-glucopyranoside

: 441310-84-5
(2S,3R,4R,5S)-1-Allyl-3,4,5-tris-benzyloxy-2-(tert-butyl-diphenyl-silanyloxymethyl)-piperidine

Guidance literature:: Multi-step reaction with 6 steps

1: 94 percent / DBU / tetrahydrofuran / 22 h

2: 85 percent / NaH; 18-crown-6 / tetrahydrofuran / 19 h / 70 °C

3: 70 percent / NBS / acetonitrile; H₂O / 2 h

4: 92 percent / NaBH₄ / ethanol / 20 h

5: 80 percent / Et₃N; DMAP / CH₂Cl₂ / 3 h / -15 °C

6: 73 percent / 39 h / 70 °C

With dmap; sodium tetrahydroborate; N-Bromosuccinimide; 18-crown-6 ether; sodium hydride; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; In tetrahydrofuran; ethanol; dichloromethane; water; acetonitrile;
DOI:10.1016/S0040-4039(02)00250-2