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

Base Information

• Chemical Name: (2S,3R)-3-[(4-nitrobenzoyl)oxy-1,4-bisbenzyloxybutan-2-yloxy]propyl pivalate
• CAS No.: 1006908-55-9
• Molecular Formula: C₃₃H₃₉NO₉
• Molecular Weight: 593.674
• Mol file: 1006908-55-9.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 1 articles about (2S,3R)-3-[(4-nitrobenzoyl)oxy-1,4-bisbenzyloxybutan-2-yloxy]propyl pivalate 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%

(2R,3S)-1,4-dibenzyloxy-3-(3-pivaloyloxypropoxy)butan-2-ol (200636-22-2) + 4-nitro-benzoic acid (62-23-7) → (2S,3R)-3-[(4-nitrobenzoyl)oxy-1,4-bisbenzyloxybutan-2-yloxy]propyl pivalate (1006908-55-9)

Guidance literature:

With triphenylphosphine; diethylazodicarboxylate; In toluene; at 20 ℃; for 20h;

DOI:10.1016/j.bmc.2006.07.039

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:

(2S,3R)-3-[(4-nitrobenzoyl)oxy-1,4-bisbenzyloxybutan-2-yloxy]propyl pivalate (1006908-55-9) → (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 13 steps

1.1: 86 percent / NaHCO₃ / methanol / 8 h / 20 °C

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

3.1: 7.78 g / p-toluenesulfonic acid monohydrate / acetone / 4 h / 20 °C

4.1: 580 mg / oxalyl chloride; dimethyl sulfoxide; triethylamine / CH₂Cl₂ / -78 - 0 °C

5.1: 330 mg / tetrahydrofuran / 3 h / -40 °C

6.1: 40 percent / Novozyme / various solvent(s) / 168 h / 30 °C

7.1: 90 percent / acetic acid / H₂O / 22 h / 20 °C

8.1: 75 percent / triphenylphosphine; diethyl azodicarboxylate / toluene / 17 h / Heating

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

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

10.1: 503 mg / NaOH / methanol; H₂O / 6 h / 20 °C

11.1: 100 percent / triethylamine / CH₂Cl₂ / 2 h / -40 °C

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

13.1: 58.4 mg / NH₄F / methanol / 4 h / Heating

With ammonium fluoride; sodium hydroxide; n-butyllithium; oxalyl dichloride; Novozyme; hydrogen; sodium hydrogencarbonate; toluene-4-sulfonic acid; acetic acid; dimethyl sulfoxide; triethylamine; triphenylphosphine; diethylazodicarboxylate; palladium dihydroxide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In tetrahydrofuran; methanol; dichloromethane; water; acetone; toluene; 4.1: Swern oxidation / 5.1: Grignard reaction;

DOI:10.1016/j.bmc.2006.07.039

upstream raw materials:

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

4-nitro-benzoic acid

Downstream raw materials:

(2S,3S)-3-(1,4-bisbenzyloxy-3-hydroxybutan-2-yloxy)propyl pivalate