2H-Pyran-3(6H)-one, 2-(phenylmethoxy)-, (2S)-

Base Information

• Chemical Name: 2H-Pyran-3(6H)-one, 2-(phenylmethoxy)-, (2S)-
• CAS No.: 391928-90-8
• Molecular Formula: C12H12O3
• Molecular Weight: 204.225
• DSSTox Substance ID: DTXSID40456183
• Nikkaji Number: J1.715.972K
• Wikidata: Q82278418
• Mol file: 391928-90-8.mol

Synonyms:2H-Pyran-3(6H)-one, 2-(phenylmethoxy)-, (2S)-;391928-90-8;DTXSID40456183;(2S)-2-(Benzyloxy)-2H-pyran-3(6H)-one

Chemical Property of 2H-Pyran-3(6H)-one, 2-(phenylmethoxy)-, (2S)-

Chemical Property:

• XLogP3: 1.5
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 3
• Exact Mass: 204.078644241
• Heavy Atom Count: 15
• Complexity: 241

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1C=CC(=O)C(O1)OCC2=CC=CC=C2
• Isomeric SMILES: C1C=CC(=O)[C@@H](O1)OCC2=CC=CC=C2

Technology Process of 2H-Pyran-3(6H)-one, 2-(phenylmethoxy)-, (2S)-

There total 13 articles about 2H-Pyran-3(6H)-one, 2-(phenylmethoxy)-, (2S)- 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: 85.0%

benzyl 3,4-dideoxy-α-L-glycero-pent-3-enopyranoside (391928-94-2) → (2S)-2-benzyloxy-2H-pyran-3-(6H)-one (391928-90-8)

Guidance literature:

With 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione; In acetonitrile; at 80 ℃; for 2.5h; enantioselective reaction;

DOI:10.1016/j.carres.2019.05.005

Reference yield: 82.0%

benzyl 2,4-di-O-acetyl-3-deoxy-β-D-glycero-pent-2-enopyranoside → (2S)-2-benzyloxy-2H-pyran-3-(6H)-one (391928-90-8)

Guidance literature:

With indium(III) chloride; benzyl alcohol; In dichloromethane; at 20 ℃; for 2h;

DOI:10.1016/j.carres.2019.05.005

Reference yield: 82.0%

1,5-anhydro-2,3,4-tri-O-acetyl-D-threo-pent-1-enitol (14125-76-9,30694-66-7,139972-99-9) + benzyl alcohol (100-51-6,185532-71-2) → (2S)-2-benzyloxy-2H-pyran-3-(6H)-one (391928-90-8)

Guidance literature:

With boron trifluoride diethyl etherate; In dichloromethane; at 5 ℃; for 0.5h;

DOI:10.1021/jo020309w

upstream raw materials:

1,5-anhydro-2,3,4-tri-O-acetyl-D-threo-pent-1-enitol

benzyl alcohol

2,3,4-tri-O-acetyl-1,5-anhydro-D-erythro-pent-1-enitol

benzyl 3,4-dideoxy-α-L-glycero-pent-3-enopyranoside

Downstream raw materials:

(3S,4aR,5S,8R,8aS)-3-benzyloxy-4a,5,8,8a-tetrahydro-5,8-methano-1H-2-benzopyran-4(3H)-one

(3S,4aS,5R,8S,8aR)-3-benzyloxy-4a,5,8,8a-tetrahydro-5,8-methano-1H-2-benzopyran-4(3H)-one

(3S,4aR,5S,8R,8aS)-3-benzyloxy-4a,5,8,8a-tetrahydro-5,8-ethano-1H-2-benzopyran-4(3H)-one

benzyl 3-deoxy-4-S-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-4-thio-β-D-erythro-pentopyranoside

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