(3S,5R)-1-ethynyl-2-methyl-3,5-bis[(vinyloxy)carbonyloxy]-1-cyclohexene

Base Information

• Chemical Name: (3S,5R)-1-ethynyl-2-methyl-3,5-bis[(vinyloxy)carbonyloxy]-1-cyclohexene
• CAS No.: 190264-67-6
• Molecular Formula: C₁₅H₁₆O₆
• Molecular Weight: 292.288
• Mol file: 190264-67-6.mol

Synonyms:(3S,5R)-1-ethynyl-2-methyl-3,5-bis[(vinyloxy)carbonyloxy]-1-cyclohexene

Chemical Property of (3S,5R)-1-ethynyl-2-methyl-3,5-bis[(vinyloxy)carbonyloxy]-1-cyclohexene

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3S,5R)-1-ethynyl-2-methyl-3,5-bis[(vinyloxy)carbonyloxy]-1-cyclohexene

There total 2 articles about (3S,5R)-1-ethynyl-2-methyl-3,5-bis[(vinyloxy)carbonyloxy]-1-cyclohexene 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: 87.0%

Vinyl chloroformate (5130-24-5) + (3S,5R)-1-ethynyl-3,5-dihydroxy-2-methylcyclohex-1-ene (113375-51-2) → (3S,5R)-1-ethynyl-2-methyl-3,5-bis[(vinyloxy)carbonyloxy]-1-cyclohexene (190264-67-6)

Guidance literature:

With pyridine; In dichloromethane; for 1h;

DOI:10.1016/j.tetasy.2004.07.052

Reference yield:

(3S,5R)-1-ethynyl-3,5-dihydroxy-2-methylcyclohex-1-ene (113375-51-2) + acetone O-<(vinyloxy)carbonyl>oxime (139705-38-7) → (3S,5R)-1-ethynyl-3-hydroxy-2-methyl-5-[(vinyloxy)carbonyloxy]-1-cyclohexene (190264-64-3) + (3S,5R)-1-ethynyl-2-methyl-3,5-bis[(vinyloxy)carbonyloxy]-1-cyclohexene (190264-67-6)

Guidance literature:

In toluene; at 30 ℃; for 23h; Product distribution; other carbonates, Pseudomonas cepacia lipase presence, other biologically active materials: Chromobacterium viscosum lipase, Candida antarctica lipase SP 435L, other solvents: THF, dioxane, other temperature and reaction time;

DOI:10.1021/jo970133b

Reference yield: 62.0%

(3S,5R)-1-ethynyl-2-methyl-3,5-bis[(vinyloxy)carbonyloxy]-1-cyclohexene (190264-67-6) → (3S,5R)-1-ethynyl-3,5-dihydroxy-2-methylcyclohex-1-ene (113375-51-2) + (3S,5R)-1-ethynyl-3-hydroxy-2-methyl-5-[(vinyloxy)carbonyloxy]-1-cyclohexene (190264-64-3) + (3S,5R)-1-ethynyl-5-hydroxy-2-methyl-3-[(vinyloxy)carbonyloxy]-1-cyclohexene (797037-94-6)

Guidance literature:

With potassium hydroxide; potassium dihydrogenphosphate; Candida rugosa lipase; In 1,4-dioxane; at 30 ℃; for 90h; pH=7.0;

DOI:10.1016/j.tetasy.2004.07.052

upstream raw materials:

(3S,5R)-1-ethynyl-3,5-dihydroxy-2-methylcyclohex-1-ene

acetone O-<(vinyloxy)carbonyl>oxime

Vinyl chloroformate

Downstream raw materials:

(3S,5R)-1-ethynyl-3,5-dihydroxy-2-methylcyclohex-1-ene

(3S,5R)-1-ethynyl-3-hydroxy-2-methyl-5-[(vinyloxy)carbonyloxy]-1-cyclohexene

(3S,5R)-1-ethynyl-5-hydroxy-2-methyl-3-[(vinyloxy)carbonyloxy]-1-cyclohexene