2H-Pyran, 3,6-dihydro-2-[(triphenylmethoxy)methyl]-, (2S)-

Base Information

• Chemical Name: 2H-Pyran, 3,6-dihydro-2-[(triphenylmethoxy)methyl]-, (2S)-
• CAS No.: 364730-56-3
• Molecular Formula: C25H24O2
• Molecular Weight: 356.464
• European Community (EC) Number: 609-250-0
• DSSTox Substance ID: DTXSID90463569
• Nikkaji Number: J1.919.675E
• Wikidata: Q82288506
• Mol file: 364730-56-3.mol

Synonyms:364730-56-3;2H-PYRAN, 3,6-DIHYDRO-2-[(TRIPHENYLMETHOXY)METHYL]-, (2S)-;DTXSID90463569

Chemical Property of 2H-Pyran, 3,6-dihydro-2-[(triphenylmethoxy)methyl]-, (2S)-

Chemical Property:

• Vapor Pressure: 6.4E-09mmHg at 25°C
• XLogP3: 5.4
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 6
• Exact Mass: 356.177630004
• Heavy Atom Count: 27
• Complexity: 407

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: C1C=CCOC1COC(C2=CC=CC=C2)(C3=CC=CC=C3)C4=CC=CC=C4
• Isomeric SMILES: C1C=CCO[C@@H]1COC(C2=CC=CC=C2)(C3=CC=CC=C3)C4=CC=CC=C4

Technology Process of 2H-Pyran, 3,6-dihydro-2-[(triphenylmethoxy)methyl]-, (2S)-

There total 7 articles about 2H-Pyran, 3,6-dihydro-2-[(triphenylmethoxy)methyl]-, (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: 79.0%

1,1',1''-[[[(2S)-4-methyl-2-(2-propen-1-yloxy)-4-penten-1-yl]-oxy]methylidyne]trisbenzene (170277-78-8) → (S)-2-trityloxymethyl-3,6-dihydro-2H-pyran (364730-56-3)

Guidance literature:

With Grubbs catalyst first generation; ethene; In dichloromethane; at 20 ℃; for 3h;

DOI:10.1016/S0957-4166(03)00325-2

Reference yield: 77.2%

trityl chloride (76-83-5) + (S)-(-)-(3,6-Dihydro-2H-pyran-2-yl)methanol (172323-66-9) → (S)-2-trityloxymethyl-3,6-dihydro-2H-pyran (364730-56-3)

Guidance literature:

With dmap; In pyridine; at 5 - 50 ℃;

DOI:10.1021/op020202a

Reference yield:

ethyl 3,6-dihydro-2H-pyran-2-carboxylate (42757-04-0) → (S)-2-trityloxymethyl-3,6-dihydro-2H-pyran (364730-56-3)

Guidance literature:

Multi-step reaction with 3 steps

1: B_. lentus protease aqueous formulations / 8 h / 20 °C / pH 7

2: lithium aluminium tetrahydride / tetrahydrofuran / 3.33 h / 0 - 12 °C / Inert atmosphere

3: dmap / pyridine / 5 - 50 °C

With dmap; lithium aluminium tetrahydride; B_. lentus protease aqueous formulations; In tetrahydrofuran; pyridine;

DOI:10.1021/op020202a

upstream raw materials:

trityl chloride

(S)-(-)-(3,6-Dihydro-2H-pyran-2-yl)methanol

1,1',1''-[[[(2S)-4-methyl-2-(2-propen-1-yloxy)-4-penten-1-yl]-oxy]methylidyne]trisbenzene

(S)-tritylglycidol

Downstream raw materials:

(3S)-3-(2-hydroxyethoxy)-4-(triphenylmethoxy)-1-butanol

(2S,4R,5R)-4,5-epoxy-2-trityloxymethyl-tetrahydropyran

(2S,4S,5S)-4,5-epoxy-2-trityloxymethyl-tetrahydropyran

1,5-anhydro-3-azido-3,4-dideoxy-5-O-trityl-D-arabino-hexitol