(6Z,9S)-6-ethylidene-9-p-toluenesulfonyloxymethyl-9-nonanolide

Base Information

• Chemical Name: (6Z,9S)-6-ethylidene-9-p-toluenesulfonyloxymethyl-9-nonanolide
• CAS No.: 138253-43-7
• Molecular Formula: C₁₉H₂₆O₅S
• Molecular Weight: 366.478
• Mol file: 138253-43-7.mol

Synonyms:(6Z,9S)-6-ethylidene-9-p-toluenesulfonyloxymethyl-9-nonanolide

Chemical Property of (6Z,9S)-6-ethylidene-9-p-toluenesulfonyloxymethyl-9-nonanolide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (6Z,9S)-6-ethylidene-9-p-toluenesulfonyloxymethyl-9-nonanolide

There total 10 articles about (6Z,9S)-6-ethylidene-9-p-toluenesulfonyloxymethyl-9-nonanolide 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: 95.0%

(6Z,9S)-6-ethylidene-9-hydroxymethyl-9-nonanolide (138253-42-6) + p-toluenesulfonyl chloride (98-59-9) → (6Z,9S)-6-ethylidene-9-p-toluenesulfonyloxymethyl-9-nonanolide (138253-43-7)

Guidance literature:

With pyridine; In dichloromethane; for 3h; Ambient temperature;

DOI:10.1016/S0040-4020(01)89442-4

Reference yield:

(4S)-4-(2-iodoethyl)-2,2-dimethyl-1,3-dioxolane (67987-67-1,98095-37-5,104596-85-2) → (6Z,9S)-6-ethylidene-9-p-toluenesulfonyloxymethyl-9-nonanolide (138253-43-7)

Guidance literature:

Multi-step reaction with 6 steps

1: 60 percent / t-BuOK / dimethylsulfoxide

2: 10percent HCl / 0.5 h / Ambient temperature

3: 84 percent / diethyl ether / 0.17 h / Ambient temperature

4: 60 percent / LiAlH₄ / diethyl ether / 0.33 h / Ambient temperature

5: 73 percent / methanesulfonyl chloride, pyridine / CH₂Cl₂ / 0.5 h / Ambient temperature

6: 95 percent / pyridine / CH₂Cl₂ / 3 h / Ambient temperature

With pyridine; hydrogenchloride; lithium aluminium tetrahydride; potassium tert-butylate; methanesulfonyl chloride; In diethyl ether; dichloromethane; dimethyl sulfoxide;

DOI:10.1016/S0040-4020(01)89442-4

Reference yield:

(-)-(1R,6R,9S)-6-<(1'R)-1'-hydroxy>ethyl-11,12-dioxatricyclo<7.2.1.01,6>dodecane (138253-39-1,138332-46-4) → (6Z,9S)-6-ethylidene-9-p-toluenesulfonyloxymethyl-9-nonanolide (138253-43-7)

Guidance literature:

Multi-step reaction with 2 steps

1: 73 percent / methanesulfonyl chloride, pyridine / CH₂Cl₂ / 0.5 h / Ambient temperature

2: 95 percent / pyridine / CH₂Cl₂ / 3 h / Ambient temperature

With pyridine; methanesulfonyl chloride; In dichloromethane;

DOI:10.1016/S0040-4020(01)89442-4

upstream raw materials:

(6Z,9S)-6-ethylidene-9-hydroxymethyl-9-nonanolide

p-toluenesulfonyl chloride

(4S)-4-(2-iodoethyl)-2,2-dimethyl-1,3-dioxolane

(-)-(1R,6R,9S)-6-acetyl-11,12-dioxatricyclo<7.2.1.0^1,6>dodecane

Downstream raw materials:

(R)-(-)-phoracantholide I

Refernces

• 1、 Nagumo,Suemune,Sakai. "Synthesis of phoracantholide I based on stereospecific fragmentation reactions". . p. 5585 - 5588. Retrieved 2007/10/02.