(2S^*,8S^*)-2-toluene-p-sulphonyloxymethyl-8-hexyloxocane

Base Information

• Chemical Name: (2S^*,8S^*)-2-toluene-p-sulphonyloxymethyl-8-hexyloxocane
• CAS No.: 142285-28-7
• Molecular Formula: C₂₁H₃₄O₄S
• Molecular Weight: 382.565
• Mol file: 142285-28-7.mol

Synonyms:

Chemical Property of (2S^*,8S^*)-2-toluene-p-sulphonyloxymethyl-8-hexyloxocane

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S^*,8S^*)-2-toluene-p-sulphonyloxymethyl-8-hexyloxocane

There total 6 articles about (2S^*,8S^*)-2-toluene-p-sulphonyloxymethyl-8-hexyloxocane 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%

(2S*,8S*)-2-hexyl-8-hydroxymethyloxocane (104514-64-9,104514-66-1) + p-toluenesulfonyl chloride (98-59-9) → (2S*,8S*)-2-toluene-p-sulphonyloxymethyl-8-hexyloxocane (142285-28-7)

Guidance literature:

With dmap; In dichloromethane; for 48h; Ambient temperature;

DOI:10.1039/P19920000083

Reference yield:

2-(methoxycarbonyl)cycloheptanone (52784-32-4) → (2S*,8S*)-2-toluene-p-sulphonyloxymethyl-8-hexyloxocane (142285-28-7)

Guidance literature:

Multi-step reaction with 5 steps

1: 1) NaH, 2) LiCl, DMSO, water / 1) DMF, oil, 40 deg C, 48 h, 2) 180 deg C, 90 min

2: 68 percent / Na₂HPO₄, peroxytrifluoroacetic acid / CH₂Cl₂ / 1) 0 deg C, 3 h, 2) room temperature, 14 h

3: pyridine / tetrahydrofuran; toluene / 1) -40 deg C, 30 min, 2) -40 deg C to room temperature, 3 h

4: 1) borane-THF, 2) 30percent H₂O₂, aq. NaOH / 1) THF, 30 min, 2) 0 deg C, 90 min

5: 84 percent / 4-dimethylaminopyridine / CH₂Cl₂ / 48 h / Ambient temperature

With pyridine; dmap; sodium hydroxide; disodium hydrogenphosphate; borane-THF; trifluoroacetyl peroxide; water; dihydrogen peroxide; sodium hydride; dimethyl sulfoxide; lithium chloride; In tetrahydrofuran; dichloromethane; toluene;

DOI:10.1039/P19920000083

Reference yield:

8-(R,S)-hexyloxocan-2-one (104514-60-5) → (2S*,8S*)-2-toluene-p-sulphonyloxymethyl-8-hexyloxocane (142285-28-7)

Guidance literature:

Multi-step reaction with 3 steps

1: pyridine / tetrahydrofuran; toluene / 1) -40 deg C, 30 min, 2) -40 deg C to room temperature, 3 h

2: 1) borane-THF, 2) 30percent H₂O₂, aq. NaOH / 1) THF, 30 min, 2) 0 deg C, 90 min

3: 84 percent / 4-dimethylaminopyridine / CH₂Cl₂ / 48 h / Ambient temperature

With pyridine; dmap; sodium hydroxide; borane-THF; dihydrogen peroxide; In tetrahydrofuran; dichloromethane; toluene;

DOI:10.1039/P19920000083

upstream raw materials:

(2S^*,8S^*)-2-hexyl-8-hydroxymethyloxocane

p-toluenesulfonyl chloride

2-(methoxycarbonyl)cycloheptanone

8-(R,S)-hexyloxocan-2-one