(2Z)-2-(((2S,4R,5R)-5-hydroxy-2-phenyl-[1,3]dioxan-4-yl)methylene)-octanoic acid tert-butyl ester

Base Information

• Chemical Name: (2Z)-2-(((2S,4R,5R)-5-hydroxy-2-phenyl-[1,3]dioxan-4-yl)methylene)-octanoic acid tert-butyl ester
• CAS No.: 881177-86-2
• Molecular Formula: C₂₃H₃₄O₅
• Molecular Weight: 390.52
• Mol file: 881177-86-2.mol

Synonyms:(2Z)-2-(((2S,4R,5R)-5-hydroxy-2-phenyl-[1,3]dioxan-4-yl)methylene)-octanoic acid tert-butyl ester

Chemical Property of (2Z)-2-(((2S,4R,5R)-5-hydroxy-2-phenyl-[1,3]dioxan-4-yl)methylene)-octanoic acid tert-butyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2Z)-2-(((2S,4R,5R)-5-hydroxy-2-phenyl-[1,3]dioxan-4-yl)methylene)-octanoic acid tert-butyl ester

There total 1 articles about (2Z)-2-(((2S,4R,5R)-5-hydroxy-2-phenyl-[1,3]dioxan-4-yl)methylene)-octanoic acid tert-butyl 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: 67.0%

C6H13CHCO2C4H9P(OC6H5)2 + 2,4-O-benzylidene-D-threose (99274-32-5) → (2Z)-2-(((2S,4R,5R)-5-hydroxy-2-phenyl-[1,3]dioxan-4-yl)methylene)-octanoic acid tert-butyl ester (881177-86-2) + (2E)-2-(((2S,4R,5R)-5-hydroxy-2-phenyl-[1,3]dioxan-4-yl)methylene)-octanoic acid tert-butyl ester

Guidance literature:

C₆H₁₃CHCO₂C₄H₉P(OC₆H₅)2; With 1,8-diazabicyclo[5.4.0]undec-7-ene; lithium chloride; In tetrahydrofuran; at -78 ℃; for 0.5h;

2,4-O-benzylidene-D-threose; In tetrahydrofuran; at -78 ℃; for 18h;

DOI:10.1002/anie.200501983

Reference yield:

(2Z)-2-(((2S,4R,5R)-5-hydroxy-2-phenyl-[1,3]dioxan-4-yl)methylene)-octanoic acid tert-butyl ester (881177-86-2) + trifluoromethylsulfonic anhydride (358-23-6) → 2-[1-((2S,4R,5R)-2-Phenyl-5-trifluoromethanesulfonyloxy-[1,3]dioxan-4-yl)-meth-(Z)-ylidene]-octanoic acid tert-butyl ester

Guidance literature:

With pyridine; In dichloromethane; at -40 ℃;

DOI:10.1002/anie.200501983

Reference yield:

(2Z)-2-(((2S,4R,5R)-5-hydroxy-2-phenyl-[1,3]dioxan-4-yl)methylene)-octanoic acid tert-butyl ester (881177-86-2) → (2Z)-2-(((2S,4R,5S)-5-(benzamido)-2-phenyl-[1,3]dioxan-4-yl)methylene)-octanoic acid tert-butyl ester (881177-92-0)

Guidance literature:

Multi-step reaction with 4 steps

1.1: pyridine / CH₂Cl₂ / -40 °C

2.1: 0.478 g / NaN₃ / CH₂Cl₂; dimethylformamide / 20 h / 20 °C

3.1: Ph₃P / tetrahydrofuran

3.2: 94 percent / H₂O / tetrahydrofuran / 74 h / 60 °C

4.1: 93 percent / Et₃N / tetrahydrofuran / 24 h

With pyridine; sodium azide; triethylamine; triphenylphosphine; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1002/anie.200501983

upstream raw materials:

2,4-O-benzylidene-D-threose

Downstream raw materials:

(2Z)-2-(((2S,4R,5S)-5-azido-2-phenyl-[1,3]dioxan-4-yl)methylene)-octanoic acid tert-butyl ester

(2Z)-2-(((2S,4R,5S)-5-(benzamido)-2-phenyl-[1,3]dioxan-4-yl)methylene)-octanoic acid tert-butyl ester

2-[1-[(2S,4R,5S)-5-((E)-Hex-2-enoylamino)-2-phenyl-[1,3]dioxan-4-yl]-meth-(Z)-ylidene]-octanoic acid tert-butyl ester

2-[1-((2S,4R,5S)-5-Hexanoylamino-2-phenyl-[1,3]dioxan-4-yl)-meth-(Z)-ylidene]-octanoic acid tert-butyl ester