(2S,3S,4R,5R,6S)-N-benzyl-3,4,5-tribenzyloxy-6-benzyloxymethyl-2-(2-propenyl)piperidine

Base Information

Chemical Name:(2S,3S,4R,5R,6S)-N-benzyl-3,4,5-tribenzyloxy-6-benzyloxymethyl-2-(2-propenyl)piperidine
CAS No.:860264-32-0
Molecular Formula:C₄₄H₄₇NO₄
Molecular Weight:653.861
Hs Code.:

Synonyms:(2S,3S,4R,5R,6S)-N-benzyl-3,4,5-tribenzyloxy-6-benzyloxymethyl-2-(2-propenyl)piperidine

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Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

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Chemical Property of (2S,3S,4R,5R,6S)-N-benzyl-3,4,5-tribenzyloxy-6-benzyloxymethyl-2-(2-propenyl)piperidine

Chemical Property:

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Technology Process of (2S,3S,4R,5R,6S)-N-benzyl-3,4,5-tribenzyloxy-6-benzyloxymethyl-2-(2-propenyl)piperidine

There total 7 articles about (2S,3S,4R,5R,6S)-N-benzyl-3,4,5-tribenzyloxy-6-benzyloxymethyl-2-(2-propenyl)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: 70.0%

: 1449009-42-0
((2S,3R,4R,5S,6S)-6-allyl-1-benzyl-3,4,5-tris(benzyloxy)piperidin-2-yl)methanol

: 100-39-0
benzyl bromide

: 860264-32-0
(2S,3S,4R,5R,6S)-N-benzyl-3,4,5-tribenzyloxy-6-benzyloxymethyl-2-(2-propenyl)piperidine

Guidance literature:: With sodium hydride; In N,N-dimethyl-formamide; mineral oil; at 20 ℃; Inert atmosphere;
DOI:10.1021/acs.orglett.9b01712

Reference yield:

: 1354826-63-3
(3R,4R,5R,6S,7S) 7-allyl-1-benzyl-4,5,6-tris(benzyloxy)azepan-3-ol

: 860264-32-0
(2S,3S,4R,5R,6S)-N-benzyl-3,4,5-tribenzyloxy-6-benzyloxymethyl-2-(2-propenyl)piperidine

Guidance literature:: Multi-step reaction with 2 steps

1: triethylamine; trifluoroacetic anhydride / toluene / 4 h / 0 - 115 °C

2: sodium hydride / N,N-dimethyl-formamide; mineral oil / 20 °C / Inert atmosphere

With sodium hydride; triethylamine; trifluoroacetic anhydride; In N,N-dimethyl-formamide; toluene; mineral oil;
DOI:10.1021/acs.orglett.9b01712

Reference yield:

: 4291-69-4,6386-24-9,6564-72-3,59531-24-7,69257-52-9,78184-89-1,78609-16-2,78609-17-3,78609-18-4,96553-53-6,104111-61-7,131347-08-5,4132-28-9
2,3,4,6-Tetra-O-benzyl-D-glucopyranose

: 860264-32-0
(2S,3S,4R,5R,6S)-N-benzyl-3,4,5-tribenzyloxy-6-benzyloxymethyl-2-(2-propenyl)piperidine

Guidance literature:: Multi-step reaction with 4 steps

1: 75 percent / 0.75 h / 110 °C

2: 85 percent / diethyl ether; tetrahydrofuran / 3.5 h / -30 °C

3: Cu(OCOCH₃)2*H₂O; acetic acid; Zn / H₂O / 1 h / 20 - 70 °C

4: pyridine; molecular sieves 4 Angstroem; MsCl / 100 °C

With pyridine; copper diacetate; 4 A molecular sieve; acetic acid; methanesulfonyl chloride; zinc; In tetrahydrofuran; diethyl ether; water;
DOI:10.1016/S0040-4020(03)00631-8