(3R,4S,5R,6R)-N-Benzyl-3,4,5-tris(benzyloxy)-6-<(benzyloxy)methyl>piperidin-2-one; Pentabenzyl-D-nojirilactam

Base Information

Chemical Name:(3R,4S,5R,6R)-N-Benzyl-3,4,5-tris(benzyloxy)-6-<(benzyloxy)methyl>piperidin-2-one; Pentabenzyl-D-nojirilactam
CAS No.:121209-13-0
Molecular Formula:C₄₁H₄₁NO₅
Molecular Weight:627.78
Hs Code.:

Synonyms:(3R,4S,5R,6R)-N-Benzyl-3,4,5-tris(benzyloxy)-6-<(benzyloxy)methyl>piperidin-2-one; Pentabenzyl-D-nojirilactam

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Chemical Property of (3R,4S,5R,6R)-N-Benzyl-3,4,5-tris(benzyloxy)-6-<(benzyloxy)methyl>piperidin-2-one; Pentabenzyl-D-nojirilactam

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Technology Process of (3R,4S,5R,6R)-N-Benzyl-3,4,5-tris(benzyloxy)-6-<(benzyloxy)methyl>piperidin-2-one; Pentabenzyl-D-nojirilactam

There total 8 articles about (3R,4S,5R,6R)-N-Benzyl-3,4,5-tris(benzyloxy)-6-<(benzyloxy)methyl>piperidin-2-one; Pentabenzyl-D-nojirilactam 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: 80.0%

: 13096-62-3
(3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-one

: 100-46-9
benzylamine

: 121209-13-0
(3R,4S,5R,6R)-N-Benzyl-3,4,5-tris(benzyloxy)-6-<(benzyloxy)methyl>piperidin-2-one; Pentabenzyl-D-nojirilactam

Guidance literature:: With 3 A molecular sieve; Amberlite IR 120 H+; In toluene; for 3h; Heating;
DOI:10.1016/S0040-4039(01)80301-4

Reference yield: 44.0%

: 100-44-7
benzyl chloride

: 77174-08-4
(3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-(benzyloxymethyl)piperidin-2-one

: 121209-13-0
(3R,4S,5R,6R)-N-Benzyl-3,4,5-tris(benzyloxy)-6-<(benzyloxy)methyl>piperidin-2-one; Pentabenzyl-D-nojirilactam

: (5R,6R)-N-Benzyl-3,5-bis(benzyloxy)-6-<(benzyloxy)methyl>-1,2,5,6-tetrahydropyridin-2-one

Guidance literature:: With potassium hydroxide; dimethyl sulfoxide; for 0.0833333h; Ambient temperature;
DOI:10.1002/hlca.19930760435

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

: 121209-13-0
(3R,4S,5R,6R)-N-Benzyl-3,4,5-tris(benzyloxy)-6-<(benzyloxy)methyl>piperidin-2-one; Pentabenzyl-D-nojirilactam

Guidance literature:: Multi-step reaction with 4 steps

1: 1.) DMSO, oxalyl chloride, 2.) Et₃N / 1a.) CH₂Cl₂, below -50, 90 min, 1b.) -40 deg C, 1c.) -10 deg C, 10 min, 1d.) -60 deg C, 2.) r.t, 1 h

2: NH₃ / diethyl ether / 0.75 h / Heating

3: 1.) Et₃N, DMSO, pyridine*SO₃, 2.) BF₃*Et₂O, Et₃SiH / 2.) MeCN, CH₂Cl₂, below 3 deg C, 10 min

4: 41 percent / KOH, DMSO / 0.08 h / Ambient temperature

With triethylsilane; potassium hydroxide; oxalyl dichloride; boron trifluoride diethyl etherate; ammonia; sulfur trioxide pyridine complex; dimethyl sulfoxide; triethylamine; In diethyl ether;
DOI:10.1002/hlca.19930760435