(3S,5R,3'S,5'R)-1,1'-diethynyl-3,3'-dihydroxy-2,2'-dimethyl-5,5'-[butan(1,4-dicarbamoyloxy)]dicyclohex-1-ene

Base Information

• Chemical Name: (3S,5R,3'S,5'R)-1,1'-diethynyl-3,3'-dihydroxy-2,2'-dimethyl-5,5'-[butan(1,4-dicarbamoyloxy)]dicyclohex-1-ene
• CAS No.: 916480-03-0
• Molecular Formula: C₂₄H₃₂N₂O₆
• Molecular Weight: 444.528

Synonyms:(3S,5R,3'S,5'R)-1,1'-diethynyl-3,3'-dihydroxy-2,2'-dimethyl-5,5'-[butan(1,4-dicarbamoyloxy)]dicyclohex-1-ene

Chemical Property of (3S,5R,3'S,5'R)-1,1'-diethynyl-3,3'-dihydroxy-2,2'-dimethyl-5,5'-[butan(1,4-dicarbamoyloxy)]dicyclohex-1-ene

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Technology Process of (3S,5R,3'S,5'R)-1,1'-diethynyl-3,3'-dihydroxy-2,2'-dimethyl-5,5'-[butan(1,4-dicarbamoyloxy)]dicyclohex-1-ene

There total 2 articles about (3S,5R,3'S,5'R)-1,1'-diethynyl-3,3'-dihydroxy-2,2'-dimethyl-5,5'-[butan(1,4-dicarbamoyloxy)]dicyclohex-1-ene 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: 39.0%

(3S,5R)-5-[N-(4-aminobutyl)carbamoyloxy]-1-ethynyl-3-hydroxy-2-methylcyclohex-1-ene (916479-99-7) + (3S,5R)-1-ethynyl-3-hydroxy-2-methyl-5-[(vinyloxy)carbonyloxy]-1-cyclohexene (190264-64-3) → (3S,5R,3'S,5'R)-1,1'-diethynyl-3,3'-dihydroxy-2,2'-dimethyl-5,5'-[butan(1,4-dicarbamoyloxy)]dicyclohex-1-ene (916480-03-0)

Guidance literature:

With dmap; In 1,4-dioxane; at 85 ℃; for 60h;

DOI:10.1016/j.bmc.2006.07.021

Reference yield:

(3S,5R)-1-ethynyl-3-hydroxy-2-methyl-5-[(vinyloxy)carbonyloxy]-1-cyclohexene (190264-64-3) → (3S,5R,3'S,5'R)-1,1'-diethynyl-3,3'-dihydroxy-2,2'-dimethyl-5,5'-[butan(1,4-dicarbamoyloxy)]dicyclohex-1-ene (916480-03-0)

Guidance literature:

Multi-step reaction with 2 steps

1: 94 percent / tetrahydrofuran / 16 h / 65 °C

2: 39 percent / 4-(dimethylamino)pyridine / dioxane / 60 h / 85 °C

With dmap; In tetrahydrofuran; 1,4-dioxane;

DOI:10.1016/j.bmc.2006.07.021

Reference yield: 93.0%

(3S,5R,3'S,5'R)-1,1'-diethynyl-3,3'-dihydroxy-2,2'-dimethyl-5,5'-[butan(1,4-dicarbamoyloxy)]dicyclohex-1-ene (916480-03-0) + tert-butyldimethylsilyl chloride (18162-48-6) → (3S,5R,3'S,5'R)-3,3'-di[(tert-butyldimethylsilyl)oxy]-1,1'-diethynyl-2,2'-dimethyl-5,5'-[butane(1,4-dicarbamoyloxy)]dicyclohex-1-ene (916480-06-3)

Guidance literature:

With 1H-imidazole; dmap; In N,N-dimethyl-formamide; at 20 ℃; for 12h;

DOI:10.1016/j.bmc.2006.07.021

upstream raw materials:

(3S,5R)-5-[N-(4-aminobutyl)carbamoyloxy]-1-ethynyl-3-hydroxy-2-methylcyclohex-1-ene

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

Downstream raw materials:

(3S,5R,3'S,5'R)-3,3'-di[(tert-butyldimethylsilyl)oxy]-1,1'-diethynyl-2,2'-dimethyl-5,5'-[butane(1,4-dicarbamoyloxy)]dicyclohex-1-ene

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