(4S,6R)-6-Benzyloxymethyl-4-methyl-4-vinyl-tetrahydro-pyran-2-one

Base Information

• Chemical Name: (4S,6R)-6-Benzyloxymethyl-4-methyl-4-vinyl-tetrahydro-pyran-2-one
• CAS No.: 130129-22-5
• Molecular Formula: C16H20 O3
• Molecular Weight: 260.3282
• DSSTox Substance ID: DTXSID90562142
• Mol file: 130129-22-5.mol

Synonyms:130129-22-5;4-ethenyl-4-methyl-6-(phenylmethoxymethyl)oxan-2-one;6-[(BENZYLOXY)METHYL]-4-ETHENYL-4-METHYLOXAN-2-ONE;(4S,6R)-6-BENZYLOXYMETHYL-4-METHYL-4-VINYL-TETRAHYDRO-PYRAN-2-ONE;DTXSID90562142

Chemical Property of (4S,6R)-6-Benzyloxymethyl-4-methyl-4-vinyl-tetrahydro-pyran-2-one

Chemical Property:

• Refractive Index: 1.549
• PSA: 35.53000
• LogP: 3.10110
• XLogP3: 3
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 5
• Exact Mass: 260.14124450
• Heavy Atom Count: 19
• Complexity: 320

Purity/Quality:

(4S,6R)-6-BENZYLOXYMETHYL-4-METHYL-4-VINYL-TETRAHYDRO-PYRAN-2-ONE 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1(CC(OC(=O)C1)COCC2=CC=CC=C2)C=C

Technology Process of (4S,6R)-6-Benzyloxymethyl-4-methyl-4-vinyl-tetrahydro-pyran-2-one

There total 3 articles about (4S,6R)-6-Benzyloxymethyl-4-methyl-4-vinyl-tetrahydro-pyran-2-one 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: 73.0%

vinyl magnesium bromide (1826-67-1) + (R)-6-benzyloxymethyl-4-methyl-5,6-dihydro-2H-pyran-2-one (130129-10-1) → (4S,6R)-6-Benzyloxymethyl-4-methyl-4-vinyl-tetrahydro-pyran-2-one (130129-22-5)

Guidance literature:

With copper(l) iodide; In tetrahydrofuran; at -30 ℃;

DOI:10.1016/S0040-4039(00)89055-3

Reference yield:

(Z)-(R)-6-Benzyloxy-5-hydroxy-3-methyl-hex-2-enoic acid methyl ester (130625-88-6) → (4S,6R)-6-Benzyloxymethyl-4-methyl-4-vinyl-tetrahydro-pyran-2-one (130129-22-5)

Guidance literature:

Multi-step reaction with 2 steps

2: 73 percent / CuI

With copper(l) iodide;

DOI:10.1246/cl.1990.1177

Reference yield:

methyl (R)-5-hydroxyhex-2-ynoate (130129-09-8) → (4S,6R)-6-Benzyloxymethyl-4-methyl-4-vinyl-tetrahydro-pyran-2-one (130129-22-5)

Guidance literature:

Multi-step reaction with 3 steps

3: 73 percent / CuI

With copper(l) iodide;

DOI:10.1246/cl.1990.1177

upstream raw materials:

vinyl magnesium bromide

(R)-6-benzyloxymethyl-4-methyl-5,6-dihydro-2H-pyran-2-one

(Z)-(R)-6-Benzyloxy-5-hydroxy-3-methyl-hex-2-enoic acid methyl ester

methyl (R)-5-hydroxyhex-2-ynoate

Downstream raw materials:

(4S,6R)-6-Benzyloxymethyl-4-methyl-4-vinyl-tetrahydro-pyran-2-ol