(2R,3R,4R,5S)-3,4,5-Tris(benzyloxy)-2-[(benzyloxy)methyl]-1-{5-[(tricyclo[3.3.1.1~3,7~]decan-1-yl)methoxy]pentyl}piperidine

Base Information

Chemical Name:(2R,3R,4R,5S)-3,4,5-Tris(benzyloxy)-2-[(benzyloxy)methyl]-1-{5-[(tricyclo[3.3.1.1~3,7~]decan-1-yl)methoxy]pentyl}piperidine
CAS No.:857254-45-6
Molecular Formula:C₅₀H₆₃NO₅
Molecular Weight:758.054
Hs Code.:
DSSTox Substance ID:DTXSID60582953
Wikidata:Q82474464

Synonyms:857254-45-6;DTXSID60582953;(2R,3R,4R,5S)-3,4,5-Tris(benzyloxy)-2-[(benzyloxy)methyl]-1-{5-[(tricyclo[3.3.1.1~3,7~]decan-1-yl)methoxy]pentyl}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 (2R,3R,4R,5S)-3,4,5-Tris(benzyloxy)-2-[(benzyloxy)methyl]-1-{5-[(tricyclo[3.3.1.1~3,7~]decan-1-yl)methoxy]pentyl}piperidine

Chemical Property:

XLogP3:9.5
Hydrogen Bond Donor Count:0
Hydrogen Bond Acceptor Count:6
Rotatable Bond Count:21
Exact Mass:757.47062411
Heavy Atom Count:56
Complexity:1050

Purity/Quality:

Safty Information:

Pictogram(s):
Hazard Codes:

MSDS Files:

Useful:

Canonical SMILES:C1C2CC3CC1CC(C2)(C3)COCCCCCN4CC(C(C(C4COCC5=CC=CC=C5)OCC6=CC=CC=C6)OCC7=CC=CC=C7)OCC8=CC=CC=C8
Isomeric SMILES:C1[C@@H]([C@H]([C@@H]([C@H](N1CCCCCOCC23CC4CC(C2)CC(C4)C3)COCC5=CC=CC=C5)OCC6=CC=CC=C6)OCC7=CC=CC=C7)OCC8=CC=CC=C8

Technology Process of (2R,3R,4R,5S)-3,4,5-Tris(benzyloxy)-2-[(benzyloxy)methyl]-1-{5-[(tricyclo[3.3.1.1~3,7~]decan-1-yl)methoxy]pentyl}piperidine

There total 15 articles about (2R,3R,4R,5S)-3,4,5-Tris(benzyloxy)-2-[(benzyloxy)methyl]-1-{5-[(tricyclo[3.3.1.1~3,7~]decan-1-yl)methoxy]pentyl}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: 100.0%

: 2,3,4,6-tetra-O-benzyl-N-[5-(adamantan-1-yl-methoxy)pentyl]-1-deoxynojirimycin (+)-di-p-toluoyl-L-tartaric acid

: 857254-45-6
2,3,4,6-tetra-O-benzyl-N-[5-(adamantan-1-yl-methoxy)-pentyl]-1-deoxynojirimycin

: C₅₀H₆₁NO₆

Guidance literature:: With sodium chloride; sodium hydroxide; In tert-butyl methyl ether; water; Inert atmosphere; Large scale;
DOI:10.1021/op700295x

Reference yield:

: 202577-32-0
5-(adamantan-1-yl-methoxy)-1-pentanal

: 69567-11-9,76738-52-8,126836-30-4
2,3,4,6-tetra-O-benzyl-1,5-dideoxy-1,5-imino-D-glucitol

: 857254-45-6
2,3,4,6-tetra-O-benzyl-N-[5-(adamantan-1-yl-methoxy)-pentyl]-1-deoxynojirimycin

Guidance literature:: 5-(adamantan-1-yl-methoxy)-1-pentanal; 2,3,4,6-tetra-O-benzyl-1,5-dideoxy-1,5-imino-D-glucitol; With acetic acid; In ethanol; at 20 ℃; for 0.25h;

With hydrogen; palladium on activated charcoal; In ethanol; at 20 ℃; for 40.5h; atmospheric pressure;
DOI:10.1021/jo061280p

Reference yield:

: 929619-00-1
5-(adamantan-1-yl-methoxy)-1-benzyloxy-pentane

: 857254-45-6
2,3,4,6-tetra-O-benzyl-N-[5-(adamantan-1-yl-methoxy)-pentyl]-1-deoxynojirimycin

Guidance literature:: Multi-step reaction with 3 steps

1.1: 97 percent / H₂ / Pd/C / ethanol / 20 h / 20 °C / 3750.3 Torr

2.1: 92 percent / oxalylchloride; DMSO; Et₃N / CH₂Cl₂ / 4 h / -78 - 20 °C

3.1: AcOH / ethanol / 0.25 h / 20 °C

3.2: H₂ / Pd/C / ethanol / 40.5 h / 20 °C / atmospheric pressure

With Chloro-oxo-acetic acid; hydrogen; acetic acid; dimethyl sulfoxide; triethylamine; palladium on activated charcoal; In ethanol; dichloromethane; 2.1: Swern oxidation;
DOI:10.1021/jo061280p