Propanoic acid, 2,2-dimethyl-, 3-[(1S,2S)-2-hydroxy-3-(phenylmethoxy)-1-[(phenylmethoxy)methyl]prop oxy]propyl ester

Base Information

• Chemical Name: Propanoic acid, 2,2-dimethyl-, 3-[(1S,2S)-2-hydroxy-3-(phenylmethoxy)-1-[(phenylmethoxy)methyl]prop oxy]propyl ester
• CAS No.: 915160-20-2
• Molecular Formula: C26H36O6
• Molecular Weight: 444.568
• Mol file: 915160-20-2.mol

Synonyms:

Chemical Property of Propanoic acid, 2,2-dimethyl-, 3-[(1S,2S)-2-hydroxy-3-(phenylmethoxy)-1-[(phenylmethoxy)methyl]prop oxy]propyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of Propanoic acid, 2,2-dimethyl-, 3-[(1S,2S)-2-hydroxy-3-(phenylmethoxy)-1-[(phenylmethoxy)methyl]prop oxy]propyl ester

There total 2 articles about Propanoic acid, 2,2-dimethyl-, 3-[(1S,2S)-2-hydroxy-3-(phenylmethoxy)-1-[(phenylmethoxy)methyl]prop oxy]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: 86.0%

(2S,3R)-3-[(4-nitrobenzoyl)oxy-1,4-bisbenzyloxybutan-2-yloxy]propyl pivalate (1006908-55-9) → (2S,3S)-3-(1,4-bisbenzyloxy-3-hydroxybutan-2-yloxy)propyl pivalate (915160-20-2)

Guidance literature:

With sodium hydrogencarbonate; In methanol; at 20 ℃; for 8h;

DOI:10.1016/j.bmc.2006.07.039

Reference yield:

(2R,3S)-1,4-dibenzyloxy-3-(3-pivaloyloxypropoxy)butan-2-ol (200636-22-2) → (2S,3S)-3-(1,4-bisbenzyloxy-3-hydroxybutan-2-yloxy)propyl pivalate (915160-20-2)

Guidance literature:

Multi-step reaction with 2 steps

1: 84 percent / triphenylphosphine; diethyl azodicarboxylate / toluene / 20 h / 20 °C

2: 86 percent / NaHCO₃ / methanol / 8 h / 20 °C

With sodium hydrogencarbonate; triphenylphosphine; diethylazodicarboxylate; In methanol; toluene;

DOI:10.1016/j.bmc.2006.07.039

Reference yield:

(2S,3S)-3-(1,4-bisbenzyloxy-3-hydroxybutan-2-yloxy)propyl pivalate (915160-20-2) → (5Z,7E)-(1R,2R,3S)-2-(3-hydroxypropoxy)-9,10-secocholesta-5,7,10(19)-triene-1,3,25-triol

Guidance literature:

Multi-step reaction with 12 steps

1.1: H₂ / Pd(OH)2 / methanol / 24 h / 20 °C

2.1: 7.78 g / p-toluenesulfonic acid monohydrate / acetone / 4 h / 20 °C

3.1: 580 mg / oxalyl chloride; dimethyl sulfoxide; triethylamine / CH₂Cl₂ / -78 - 0 °C

4.1: 330 mg / tetrahydrofuran / 3 h / -40 °C

5.1: 40 percent / Novozyme / various solvent(s) / 168 h / 30 °C

6.1: 90 percent / acetic acid / H₂O / 22 h / 20 °C

7.1: 75 percent / triphenylphosphine; diethyl azodicarboxylate / toluene / 17 h / Heating

8.1: n-BuLi / tetrahydrofuran / 0.5 h / -78 °C

8.2: BF₃*Et₂O / tetrahydrofuran / 1 h / -78 °C

9.1: 503 mg / NaOH / methanol; H₂O / 6 h / 20 °C

10.1: 100 percent / triethylamine / CH₂Cl₂ / 2 h / -40 °C

11.1: triethylamine / (Ph₃P)4Pd / toluene / 2 h / Heating

12.1: 58.4 mg / NH₄F / methanol / 4 h / Heating

With ammonium fluoride; sodium hydroxide; n-butyllithium; oxalyl dichloride; Novozyme; hydrogen; toluene-4-sulfonic acid; acetic acid; dimethyl sulfoxide; triethylamine; triphenylphosphine; diethylazodicarboxylate; palladium dihydroxide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In tetrahydrofuran; methanol; dichloromethane; water; acetone; toluene; 3.1: Swern oxidation / 4.1: Grignard reaction;

DOI:10.1016/j.bmc.2006.07.039

upstream raw materials:

(2S,3R)-3-[(4-nitrobenzoyl)oxy-1,4-bisbenzyloxybutan-2-yloxy]propyl pivalate

(2R,3S)-1,4-dibenzyloxy-3-(3-pivaloyloxypropoxy)butan-2-ol