2-Piperidinone, 3,4,5-tris(phenylmethoxy)-6-[(phenylmethoxy)methyl]-, (3R,4S,5R,6R)-

Base Information

• Chemical Name: 2-Piperidinone, 3,4,5-tris(phenylmethoxy)-6-[(phenylmethoxy)methyl]-, (3R,4S,5R,6R)-
• CAS No.: 77174-08-4
• Molecular Formula: C₃₄H₃₅NO₅
• Molecular Weight: 537.656
• ChEMBL ID: CHEMBL3393675
• DSSTox Substance ID: DTXSID90471285
• Nikkaji Number: J707.127B
• Wikidata: Q82299764
• Mol file: 77174-08-4.mol

Synonyms:77174-08-4;CHEMBL3393675;2-PIPERIDINONE, 3,4,5-TRIS(PHENYLMETHOXY)-6-[(PHENYLMETHOXY)METHYL]-, (3R,4S,5R,6R)-;2,3,4,6-TETRA-O-BENZYL-D-GLUCONO-1,5-LACTAM;(3R,4S,5R,6R)-3,4,5-tris(phenylmethoxy)-6-(phenylmethoxymethyl)piperidin-2-one;DTXSID90471285;BDBM50061159;AG-H-08425

Chemical Property of 2-Piperidinone, 3,4,5-tris(phenylmethoxy)-6-[(phenylmethoxy)methyl]-, (3R,4S,5R,6R)-

Chemical Property:

• XLogP3: 5
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 13
• Exact Mass: 537.25152322
• Heavy Atom Count: 40
• Complexity: 709

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C(C=C1)COCC2C(C(C(C(=O)N2)OCC3=CC=CC=C3)OCC4=CC=CC=C4)OCC5=CC=CC=C5
• Isomeric SMILES: C1=CC=C(C=C1)COC[C@@H]2[C@H]([C@@H]([C@H](C(=O)N2)OCC3=CC=CC=C3)OCC4=CC=CC=C4)OCC5=CC=CC=C5

Technology Process of 2-Piperidinone, 3,4,5-tris(phenylmethoxy)-6-[(phenylmethoxy)methyl]-, (3R,4S,5R,6R)-

There total 15 articles about 2-Piperidinone, 3,4,5-tris(phenylmethoxy)-6-[(phenylmethoxy)methyl]-, (3R,4S,5R,6R)- 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: 98.0%

(3R,4S,5S,6R)-6-Hydroxy-3,4,5-tris(benzyloxy)-6-<(benzyloxy)methyl>piperidin-2-one (76738-51-7) → (3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-(benzyloxymethyl)piperidin-2-one (77174-08-4)

Guidance literature:

With triethylsilane; boron trifluoride diethyl etherate; In dichloromethane; acetonitrile;

DOI:10.1002/hlca.19930760435

Reference yield: 98.0%

(3R,4S,5S,6S)-6-Hydroxy-3,4,5-tris(benzyloxy)-6-<(benzyloxy)methyl>piperidin-2-one (76670-95-6) → (3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-(benzyloxymethyl)piperidin-2-one (77174-08-4)

Guidance literature:

With triethylsilane; boron trifluoride diethyl etherate; In dichloromethane; acetonitrile;

DOI:10.1002/hlca.19930760435

Reference yield: 79.0%

2,3,4,6-tetra-O-benzyl-D-glucono-δ-lactam → (3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-(benzyloxymethyl)piperidin-2-one (77174-08-4)

Guidance literature:

With sodium cyanoborohydride; In formic acid; acetonitrile; for 2h; Ambient temperature;

DOI:10.1016/S0040-4020(01)86715-6

upstream raw materials:

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

2,3,4,6-tetra-O-benzyl-D-gluconamide

2,3,4,6-tetra-O-benzyl-5-dehydro-5-oxo-D-gluconamide

(3R,4S,5S,6R)-6-Hydroxy-3,4,5-tris(benzyloxy)-6-<(benzyloxy)methyl>piperidin-2-one

Downstream raw materials:

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

nojirimycin-δ-lactam

2,3,4,6-tetra-O-benzyl-1,5-dideoxy-1,5-imino-D-glucitol

2,3,4,6-tetra-O-benzyl-D-mannothiolactam