Acetic acid (2S,3R)-2,3-dihydroxy-3-phenyl-propyl ester

Base Information

• Chemical Name: Acetic acid (2S,3R)-2,3-dihydroxy-3-phenyl-propyl ester
• CAS No.: 163748-92-3
• Molecular Formula: C₁₁H₁₄O₄
• Molecular Weight: 210.23
• Mol file: 163748-92-3.mol

Synonyms:Acetic acid (2S,3R)-2,3-dihydroxy-3-phenyl-propyl ester

Chemical Property of Acetic acid (2S,3R)-2,3-dihydroxy-3-phenyl-propyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Acetic acid (2S,3R)-2,3-dihydroxy-3-phenyl-propyl ester

There total 1 articles about Acetic acid (2S,3R)-2,3-dihydroxy-3-phenyl-propyl ester 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: 84.0%

(2S,3R)-3-acetoxyl-3-phenyl-1,2-propanediol (162466-12-8) → Acetic acid (2S,3R)-2,3-dihydroxy-3-phenyl-propyl ester (163748-92-3)

Guidance literature:

With hydrogenchloride; silica gel; In tetrahydrofuran; Ambient temperature;

DOI:10.1039/c39950000743

Reference yield:

Acetic acid (2S,3R)-2,3-dihydroxy-3-phenyl-propyl ester (163748-92-3) → (5S,6R)-5-hydroxy-6-<(1R,2R)-1,2-isopropylidenyloxy-2-phenylethyl>-5,6-dihydropyran-2-one (162466-16-2)

Guidance literature:

Multi-step reaction with 6 steps

1: p-TsOH / CH₂Cl₂ / 8 h / Ambient temperature

2: 15percent NaOH / tetrahydrofuran; H₂O / Ambient temperature

3: Me₂SO, (COCl)2, Et₃N / CH₂Cl₂ / -78 - -20 °C

4: tetrahydrofuran / -78 - -30 °C

5: 84 percent / TBHP, VO(acac)2 / CH₂Cl₂ / 0 °C

6: 1) CrO₃, 2) NaBH(OAc)3 / 1) HOAc, 25 deg C to 30 deg C, 15 min, 2) iPrOH, HOAc, -10 deg C to r.t.

With chromium(VI) oxide; tert.-butylhydroperoxide; sodium hydroxide; oxalyl dichloride; bis(acetylacetonate)oxovanadium; sodium tris(acetoxy)borohydride; toluene-4-sulfonic acid; dimethyl sulfoxide; triethylamine; In tetrahydrofuran; dichloromethane; water;

DOI:10.1039/c39950000743

Reference yield:

Acetic acid (2S,3R)-2,3-dihydroxy-3-phenyl-propyl ester (163748-92-3) → (4R,5R)-cis-2,2-dimethyl-5-phenyl-1,3-dioxolan-4-carbaldehyde (130718-77-3)

Guidance literature:

Multi-step reaction with 3 steps

1: p-TsOH / CH₂Cl₂ / 8 h / Ambient temperature

2: 15percent NaOH / tetrahydrofuran; H₂O / Ambient temperature

3: Me₂SO, (COCl)2, Et₃N / CH₂Cl₂ / -78 - -20 °C

With sodium hydroxide; oxalyl dichloride; toluene-4-sulfonic acid; dimethyl sulfoxide; triethylamine; In tetrahydrofuran; dichloromethane; water;

DOI:10.1039/c39950000743

upstream raw materials:

(2S,3R)-3-acetoxyl-3-phenyl-1,2-propanediol

Downstream raw materials:

(4S-cis)-5-phenyl-2,2-dimethyl-1,3-dioxolane-4-methanol acetate

(4R,5R)-cis-2,2-dimethyl-5-phenyl-1,3-dioxolan-4-carbaldehyde

(6R,7R,8R)-goniodiol-8-monoacetate

7,8-di-O-acetyl-goniodiol