(+)-(4R,cis)(Z)-2,2-dimethyl-5-(4-carbethoxy-1-butenyl)-1,3-dioxolane-4-methanol p-toluenesulfonate

Base Information

• Chemical Name: (+)-(4R,cis)(Z)-2,2-dimethyl-5-(4-carbethoxy-1-butenyl)-1,3-dioxolane-4-methanol p-toluenesulfonate
• CAS No.: 119011-35-7
• Molecular Formula: C₂₀H₂₈O₇S
• Molecular Weight: 412.504
• Mol file: 119011-35-7.mol

Synonyms:(+)-(4R,cis)(Z)-2,2-dimethyl-5-(4-carbethoxy-1-butenyl)-1,3-dioxolane-4-methanol p-toluenesulfonate

Chemical Property of (+)-(4R,cis)(Z)-2,2-dimethyl-5-(4-carbethoxy-1-butenyl)-1,3-dioxolane-4-methanol p-toluenesulfonate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (+)-(4R,cis)(Z)-2,2-dimethyl-5-(4-carbethoxy-1-butenyl)-1,3-dioxolane-4-methanol p-toluenesulfonate

There total 3 articles about (+)-(4R,cis)(Z)-2,2-dimethyl-5-(4-carbethoxy-1-butenyl)-1,3-dioxolane-4-methanol p-toluenesulfonate 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: 85.0%

(+)-(4R,cis)(Z)-2,2-dimethyl-5-(4-carbethoxy-1-butenyl)-1,3-dioxolane-4-methanol (119011-34-6) + p-toluenesulfonyl chloride (98-59-9) → (+)-(4R,cis)(Z)-2,2-dimethyl-5-(4-carbethoxy-1-butenyl)-1,3-dioxolane-4-methanol p-toluenesulfonate (119011-35-7)

Guidance literature:

With dmap; triethylamine; In dichloromethane; for 20h; Ambient temperature;

DOI:10.1021/ja00189a034

Reference yield:

2,3-O-isopropylidene-D-erythrose (189996-60-9) → (+)-(4R,cis)(Z)-2,2-dimethyl-5-(4-carbethoxy-1-butenyl)-1,3-dioxolane-4-methanol p-toluenesulfonate (119011-35-7)

Guidance literature:

Multi-step reaction with 2 steps

1: 58 percent / KN(SiMe₃)2 / tetrahydrofuran / 1.) 0 deg C, 30 min, 2.) - 78 deg C, 3.) room temp., overnight

2: 85 percent / triethylamine, N,N-dimethyl-4-aminopyridine / CH₂Cl₂ / 20 h / Ambient temperature

With dmap; potassium hexamethylsilazane; triethylamine; In tetrahydrofuran; dichloromethane;

DOI:10.1021/ja00189a034

Reference yield:

(3-ethoxycarbonylpropyl)triphenylphosphonium bromide (50479-11-3) → (+)-(4R,cis)(Z)-2,2-dimethyl-5-(4-carbethoxy-1-butenyl)-1,3-dioxolane-4-methanol p-toluenesulfonate (119011-35-7)

Guidance literature:

Multi-step reaction with 2 steps

1: 58 percent / KN(SiMe₃)2 / tetrahydrofuran / 1.) 0 deg C, 30 min, 2.) - 78 deg C, 3.) room temp., overnight

2: 85 percent / triethylamine, N,N-dimethyl-4-aminopyridine / CH₂Cl₂ / 20 h / Ambient temperature

With dmap; potassium hexamethylsilazane; triethylamine; In tetrahydrofuran; dichloromethane;

DOI:10.1021/ja00189a034

upstream raw materials:

(+)-(4R,cis)(Z)-2,2-dimethyl-5-(4-carbethoxy-1-butenyl)-1,3-dioxolane-4-methanol

p-toluenesulfonyl chloride

2,3-O-isopropylidene-D-erythrose

(3-ethoxycarbonylpropyl)triphenylphosphonium bromide

Downstream raw materials:

(3aR,9R,9aR,9bS)-octahydro-2,2-dimethyl-[1,3]dioxolo[4,5-a]indolizin-9-ol

swainsonine