(4S,6R,E)-4-hydroxy-6-(2-phenylethenyl)-tetrahydropyran-2-one

Base Information

• Chemical Name: (4S,6R,E)-4-hydroxy-6-(2-phenylethenyl)-tetrahydropyran-2-one
• CAS No.: 70670-14-3
• Molecular Formula: C₁₃H₁₄O₃
• Molecular Weight: 218.252
• Mol file: 70670-14-3.mol

Synonyms:(4S,6R,E)-4-hydroxy-6-(2-phenylethenyl)-tetrahydropyran-2-one

Chemical Property of (4S,6R,E)-4-hydroxy-6-(2-phenylethenyl)-tetrahydropyran-2-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (4S,6R,E)-4-hydroxy-6-(2-phenylethenyl)-tetrahydropyran-2-one

There total 36 articles about (4S,6R,E)-4-hydroxy-6-(2-phenylethenyl)-tetrahydropyran-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: 82.0%

methyl (5R,E)-(tert-butyldimethylsilyloxy)-3-hydroxy-7-phenylhept-6-enoate → (4R,6R,1'E)-4-hydroxy-6-(2'-phenylvinyl)-3,4,5,6-tetrahydro-2H-pyran-2-one (70633-86-2) + (4S,6R,E)-4-hydroxy-6-(2-phenylethenyl)-tetrahydropyran-2-one (70670-14-3) + methyl (5R,E)-3,5-dihydroxy-7-phenylhept-6-enoate

Guidance literature:

With water; acetic acid; In tetrahydrofuran; for 24h; Ambient temperature;

DOI:10.1248/cpb.42.839

Reference yield: 48.0%

methyl (5R,E)-3,5-dihydroxy-7-phenylhept-6-enoate → (4R,6R,1'E)-4-hydroxy-6-(2'-phenylvinyl)-3,4,5,6-tetrahydro-2H-pyran-2-one (70633-86-2) + (4S,6R,E)-4-hydroxy-6-(2-phenylethenyl)-tetrahydropyran-2-one (70670-14-3)

Guidance literature:

With acetic acid; at 50 ℃; for 20h;

DOI:10.1248/cpb.42.839

Reference yield:

3,5-dideoxy-1,2-O-isopropylidene-α-D-erythro-hexofuranose (58475-20-0) → (4S,6R,E)-4-hydroxy-6-(2-phenylethenyl)-tetrahydropyran-2-one (70670-14-3)

Guidance literature:

Multi-step reaction with 4 steps

1: pyridinium dichromate / dimethylformamide / 24 h / Ambient temperature

2: dimethylformamide; diethyl ether / 0 °C

3: 87 percent / water / Amberlit IR 120 resin (H⁺ form) / Ambient temperature

4: 1.) Na-methylsulphinylmethanide / 1.) Me₂SO, heating, 2.) Me₂SO, 3 h, room t.

With dipyridinium dichromate; dimsylsodium; water; Amberlit IR 120 resin (H⁺ form); In diethyl ether; N,N-dimethyl-formamide;

upstream raw materials:

benzyltriphenylphosphonium chloride

methyl 3,5-dideoxy-β-D-glucofuranuronate

methyl (E,3S^*,5R^*)-3,5-dihydroxy-7-phenyl-6-heptenoate

methyl (3S,5R,6E)-7-phenyl-3,5-isopropylidenedioxy-6-heptenoate

Downstream raw materials:

(R)-goniothalamin

(4S,6R)-3,4,5,6-tetrahydro-6-(2-phenylethenyl)-4-dimethyl-t-butylsilyloxy-2H-pyran-2-one

(R)-4-(tert-Butyl-dimethyl-silanyloxy)-6-((E)-styryl)-tetrahydro-pyran-2-one

(4S,6R)-4-(tert-Butyl-dimethyl-silanyloxy)-6-((Z)-styryl)-tetrahydro-pyran-2-one