(2R,3S,4R,5R,6R)-2-allyl-3,4,5-tris(benzyloxy)-6-(benzyloxymethyl)piperidine

Base Information

• Chemical Name: (2R,3S,4R,5R,6R)-2-allyl-3,4,5-tris(benzyloxy)-6-(benzyloxymethyl)piperidine
• CAS No.: 950599-08-3
• Molecular Formula: C₃₇H₄₁NO₄
• Molecular Weight: 563.737
• Mol file: 950599-08-3.mol

Synonyms:(2R,3S,4R,5R,6R)-2-allyl-3,4,5-tris(benzyloxy)-6-(benzyloxymethyl)piperidine

Chemical Property of (2R,3S,4R,5R,6R)-2-allyl-3,4,5-tris(benzyloxy)-6-(benzyloxymethyl)piperidine

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2R,3S,4R,5R,6R)-2-allyl-3,4,5-tris(benzyloxy)-6-(benzyloxymethyl)piperidine

There total 10 articles about (2R,3S,4R,5R,6R)-2-allyl-3,4,5-tris(benzyloxy)-6-(benzyloxymethyl)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:

allyltributylstanane (24850-33-7) + 1,N-didehydro-2,3,4,6-tetra-O-benzyl-deoxynojirimycin → (2S,3S,4R,5R,6R)-2-allyl-3,4,5-tris(benzyloxy)-6-(benzyloxymethyl)piperidine (1570183-94-6) + (2R,3S,4R,5R,6R)-2-allyl-3,4,5-tris(benzyloxy)-6-(benzyloxymethyl)piperidine (950599-08-3)

Guidance literature:

1,N-didehydro-2,3,4,6-tetra-O-benzyl-deoxynojirimycin; With ytterbium(III) triflate; In tetrahydrofuran; at -25 ℃; for 0.166667h;

allyltributylstanane; In tetrahydrofuran; at -25 - 20 ℃;

DOI:10.1016/j.tet.2014.01.039

Reference yield:

(1R)-2,3,4,6-tetra-O-benzyl-N-[(4-methoxybenzyl)amino]-1-C-(prop-2-enyl)-1-deoxynojirimycin (1222826-97-2) → (2R,3S,4R,5R,6R)-2-allyl-3,4,5-tris(benzyloxy)-6-(benzyloxymethyl)piperidine (950599-08-3)

Guidance literature:

With ammonium cerium (IV) nitrate; In tetrahydrofuran; water; at 0 ℃; for 3h;

DOI:10.1002/ejoc.200901208

Reference yield:

(3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-(benzyloxymethyl)piperidin-2-one (77174-08-4) → (2S,3S,4R,5R,6R)-2-allyl-3,4,5-tris(benzyloxy)-6-(benzyloxymethyl)piperidine (1570183-94-6) + (2R,3S,4R,5R,6R)-2-allyl-3,4,5-tris(benzyloxy)-6-(benzyloxymethyl)piperidine (950599-08-3)

Guidance literature:

Multi-step reaction with 2 steps

1.1: Schwartz's reagent / tetrahydrofuran / 0.75 h / -25 - 20 °C / Inert atmosphere

2.1: ytterbium(III) triflate / tetrahydrofuran / 0.17 h / -25 °C

2.2: -25 - 20 °C

With Schwartz's reagent; ytterbium(III) triflate; In tetrahydrofuran;

DOI:10.1016/j.tet.2014.01.039

upstream raw materials:

(2R,3R,4R,5S,6R)-N-benzyl-3,4,5-tris(benzyloxy)-2-benzyloxymethyl-6-(prop-2-enyl)piperidine

2,3,4,6-Tetra-O-benzyl-D-glucopyranose

N-benzyl-2,3,4,6-tetra-O-benzyl-D-glucopyranosylamine

(3S,4R,5S,6R)-6-Benzylamino-1,3,4,5-tetrakis-benzyloxy-non-8-en-2-one