(-)-(2R,3S)-3-(Benzyloxy)-2-<(benzyloxy)methyl>-2,3-dihydro-4H-pyran-4-one

Base Information

• Chemical Name: (-)-(2R,3S)-3-(Benzyloxy)-2-<(benzyloxy)methyl>-2,3-dihydro-4H-pyran-4-one
• CAS No.: 149561-64-8
• Molecular Formula: C₂₀H₂₀O₄
• Molecular Weight: 324.376
• Mol file: 149561-64-8.mol

Synonyms:(-)-(2R,3S)-3-(Benzyloxy)-2-<(benzyloxy)methyl>-2,3-dihydro-4H-pyran-4-one

Chemical Property of (-)-(2R,3S)-3-(Benzyloxy)-2-<(benzyloxy)methyl>-2,3-dihydro-4H-pyran-4-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (-)-(2R,3S)-3-(Benzyloxy)-2-<(benzyloxy)methyl>-2,3-dihydro-4H-pyran-4-one

There total 14 articles about (-)-(2R,3S)-3-(Benzyloxy)-2-<(benzyloxy)methyl>-2,3-dihydro-4H-pyran-4-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: 86.0%

3,4,6-tri-O-benzyl-D-galactal (80040-79-5) → (-)-(2R,3S)-3-(Benzyloxy)-2-<(benzyloxy)methyl>-2,3-dihydro-4H-pyran-4-one (149561-64-8)

Guidance literature:

With [bis(acetoxy)iodo]benzene; toluene-4-sulfonic acid; In acetonitrile; at 20 ℃; for 0.75h;

DOI:10.1016/S0040-4039(02)00872-9

Reference yield: 58.0%

3,4,6-tri-O-benzyl-D-galactal (80040-79-5) → (-)-(2R,3S)-3-(Benzyloxy)-2-<(benzyloxy)methyl>-2,3-dihydro-4H-pyran-4-one (149561-64-8) + (-)-(2R,3S,4R,5R)-5-[(Benzyloxy)methyl]-2,4-bis(benzyloxy)-3-(1',1'-bis(benzyloxy)methyl)tetrahydrofuran + (+)-(2S,3S,4R,5R)-5-[(Benzyloxy)methyl]-2,4-bis(benzyloxy)-3-(1',1'-bis(benzyloxy)methyl)tetrahydrofuran

Guidance literature:

With [hydroxy(tosyloxy)iodo]benzene; In acetonitrile;

DOI:10.1002/jlac.199719971015

Reference yield: 14.0%

n-Pent-4-enyl alcohol (821-09-0) + 3-O-carbamoyl-4,6-di-O-benzyl-D-galactal → 4-pentenyl 2-amino-2-N,3-O-carbonyl-2-deoxy-4,6-di-O-benzyl-α-D-talopyranoside + (-)-(2R,3S)-3-(Benzyloxy)-2-<(benzyloxy)methyl>-2,3-dihydro-4H-pyran-4-one (149561-64-8)

Guidance literature:

With rhodium(II) acetate dimer; iodosylbenzene; In dichloromethane; at 23 ℃; for 4h; diastereoselective reaction; Molecular sieve;

DOI:10.1021/acs.joc.8b00893

upstream raw materials:

3,4,6-tri-O-benzyl-D-galactal

4,6-di-O-benzyl-D-galactal

benzyl bromide

D-galactal

Downstream raw materials:

4,6-di-O-benzyl-D-galactal

5-((1S,2R)-1,3-Bis-benzyloxy-2-hydroxy-propyl)-4,5-dihydro-isoxazol-5-ol

(2R,3S,5R,6R)-3-Benzyloxy-2-benzyloxymethyl-6-(2-[1,3]dioxan-2-yl-ethyl)-5-methyl-tetrahydro-pyran-4-one

((5S,6R)-5-Benzyloxy-6-benzyloxymethyl-4-oxo-5,6-dihydro-4H-pyran-3-yl)-phosphonic acid diethyl ester