Benzyl (4aR,7S,8R,8aR)-7,8-bis(acetyloxy)-2-phenylhexahydro-2H,5H-[1,3]dioxino[5,4-b]pyridine-5-carboxylate

Base Information

Chemical Name:Benzyl (4aR,7S,8R,8aR)-7,8-bis(acetyloxy)-2-phenylhexahydro-2H,5H-[1,3]dioxino[5,4-b]pyridine-5-carboxylate
CAS No.:153373-52-5
Molecular Formula:C₂₅H₂₇NO₈
Molecular Weight:469.491
Hs Code.:
DSSTox Substance ID:DTXSID00707143
Mol file:153373-52-5.mol

Synonyms:153373-52-5;N-Benzyloxycarbonyl-4,6-O-phenylmethylene Deoxynojirimycin Diacetate;benzyl (4aR,7S,8R,8aR)-7,8-diacetyloxy-2-phenyl-4,4a,6,7,8,8a-hexahydro-[1,3]dioxino[5,4-b]pyridine-5-carboxylate;Benzyl (4aR,7S,8R,8aR)-7,8-bis(acetyloxy)-2-phenylhexahydro-2H,5H-[1,3]dioxino[5,4-b]pyridine-5-carboxylate;SCHEMBL9230633;DTXSID00707143;GQWUJUIVSOFDOW-QXNXEDLHSA-N

Suppliers and Price of Benzyl (4aR,7S,8R,8aR)-7,8-bis(acetyloxy)-2-phenylhexahydro-2H,5H-[1,3]dioxino[5,4-b]pyridine-5-carboxylate

Supply Marketing:

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

Manufacturers and distributors:

Manufacture/Brand
Chemicals and raw materials
Packaging
price

Usbiological
N-Benzyloxycarbonyl-4,6-O-phenylmethylene Deoxynojirimycin Diacetate
2.5mg
$ 496.00

TRC
N-Benzyloxycarbonyl-4,6-O-phenylmethyleneDeoxynojirimycinDiacetate
2.5mg
$ 215.00

TRC
N-Benzyloxycarbonyl-4,6-O-phenylmethyleneDeoxynojirimycinDiacetate
25mg
$ 1695.00

Medical Isotopes, Inc.
N-Benzyloxycarbonyl-4,6-O-phenylmethyleneDeoxynojirimycinDiacetate
25 mg
$ 2400.00

Total 4 raw suppliers

Chemical Property of Benzyl (4aR,7S,8R,8aR)-7,8-bis(acetyloxy)-2-phenylhexahydro-2H,5H-[1,3]dioxino[5,4-b]pyridine-5-carboxylate

Chemical Property:

Melting Point:157-159oC
Storage Temp.:Refrigerator, under inert atmosphere
Solubility.:Methanol (Slightly)
XLogP3:2.5
Hydrogen Bond Donor Count:0
Hydrogen Bond Acceptor Count:8
Rotatable Bond Count:8
Exact Mass:469.17366682
Heavy Atom Count:34
Complexity:718

Purity/Quality:

99% ^*data from raw suppliers

N-Benzyloxycarbonyl-4,6-O-phenylmethylene Deoxynojirimycin Diacetate ^*data from reagent suppliers

Safty Information:

Pictogram(s):
Hazard Codes:

MSDS Files:

Useful:

Canonical SMILES:CC(=O)OC1CN(C2COC(OC2C1OC(=O)C)C3=CC=CC=C3)C(=O)OCC4=CC=CC=C4
Isomeric SMILES:CC(=O)O[C@H]1CN([C@@H]2COC(O[C@H]2[C@@H]1OC(=O)C)C3=CC=CC=C3)C(=O)OCC4=CC=CC=C4

Technology Process of Benzyl (4aR,7S,8R,8aR)-7,8-bis(acetyloxy)-2-phenylhexahydro-2H,5H-[1,3]dioxino[5,4-b]pyridine-5-carboxylate

There total 1 articles about Benzyl (4aR,7S,8R,8aR)-7,8-bis(acetyloxy)-2-phenylhexahydro-2H,5H-[1,3]dioxino[5,4-b]pyridine-5-carboxylate 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%

: 108-24-7
acetic anhydride

: 138381-83-6
4,6-O-(R-Benzylidene)-N-benzyloxycarbonyl-1,5-dideoxy-1,5-imino-D-glucitol

: 153373-52-5
2,3-di-O-acetyl-4,6-O-benzylidene-1,5-benzyloxycarbonylimino-1,5-dideoxy-D-glucitol

Guidance literature:: With pyridine;
DOI:10.1016/0008-6215(95)00068-5

Reference yield: 100.0%

: 153373-52-5
2,3-di-O-acetyl-4,6-O-benzylidene-1,5-benzyloxycarbonylimino-1,5-dideoxy-D-glucitol

: 153373-53-6
2,3-di-O-acetyl-1,5-benzyloxycarbonylimino-1,5-dideoxy-D-glucitol

Guidance literature:: With acetic acid; at 45 ℃; for 6h;
DOI:10.1016/0008-6215(95)00068-5

Reference yield:

: 153373-52-5
2,3-di-O-acetyl-4,6-O-benzylidene-1,5-benzyloxycarbonylimino-1,5-dideoxy-D-glucitol

: 172139-94-5
(2R,3S,4R,5S)-3,4,5-Trihydroxy-2-hydroxymethyl-piperidine-1-carboxylic acid benzyl ester

Guidance literature:: Multi-step reaction with 6 steps

1: 100 percent / 80percent aq. AcOH / 6 h / 45 °C

2: 93 percent / pyridine / 20 °C

3: pyridine / CH₂Cl₂ / 3 h / -15 °C

4: 18-crown-6 / acetonitrile / Ambient temperature

5: 100 percent / NaOCH₃ / methanol / 2.5 h / 0 °C

6: 215 mg / BF₃*Et₂O / CH₂Cl₂ / 2 h / Ambient temperature

With pyridine; 18-crown-6 ether; boron trifluoride diethyl etherate; sodium methylate; acetic acid; In methanol; dichloromethane; acetonitrile;
DOI:10.1016/0008-6215(95)00068-5