<1R,1α(S^*),3α(E)>-1-Cyano-1-(3-phenoxyphenyl)methyl 2,2-Dimethyl-3-<3-tert-butoxy-2-(tert-butylsulfonyl)-3-oxo-1-propenyl>cyclopropanecarboxylate

Base Information

• Chemical Name: <1R,1α(S^*),3α(E)>-1-Cyano-1-(3-phenoxyphenyl)methyl 2,2-Dimethyl-3-<3-tert-butoxy-2-(tert-butylsulfonyl)-3-oxo-1-propenyl>cyclopropanecarboxylate
• CAS No.: 130051-21-7
• Molecular Formula: C₃₁H₃₇NO₇S
• Molecular Weight: 567.703

Synonyms:<1R,1α(S^*),3α(E)>-1-Cyano-1-(3-phenoxyphenyl)methyl 2,2-Dimethyl-3-<3-tert-butoxy-2-(tert-butylsulfonyl)-3-oxo-1-propenyl>cyclopropanecarboxylate

Chemical Property of <1R,1α(S^*),3α(E)>-1-Cyano-1-(3-phenoxyphenyl)methyl 2,2-Dimethyl-3-<3-tert-butoxy-2-(tert-butylsulfonyl)-3-oxo-1-propenyl>cyclopropanecarboxylate

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Technology Process of <1R,1α(S^*),3α(E)>-1-Cyano-1-(3-phenoxyphenyl)methyl 2,2-Dimethyl-3-<3-tert-butoxy-2-(tert-butylsulfonyl)-3-oxo-1-propenyl>cyclopropanecarboxylate

There total 5 articles about <1R,1α(S^*),3α(E)>-1-Cyano-1-(3-phenoxyphenyl)methyl 2,2-Dimethyl-3-<3-tert-butoxy-2-(tert-butylsulfonyl)-3-oxo-1-propenyl>cyclopropanecarboxylate 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: 74.0%

(1R,1α,3α)-6,6-Dimethyl-4-<2-tert-butoxy-2-oxo-1-(tert-butylsulfonyl)ethyl>-3-oxabicyclo<3.1.0>hexan-2-one (130051-19-3) + (S)-m-phenoxybenzaldehyde cyanohydrin (39515-47-4,52315-06-7,61826-76-4,71962-66-8) → <1R,1α(S*),3α(E)>-1-Cyano-1-(3-phenoxyphenyl)methyl 2,2-Dimethyl-3-<3-tert-butoxy-2-(tert-butylsulfonyl)-3-oxo-1-propenyl>cyclopropanecarboxylate (130051-21-7)

Guidance literature:

With dmap; dicyclohexyl-carbodiimide; In dichloromethane; for 18h; Ambient temperature;

DOI:10.1021/jo00028a034

Reference yield:

bromoacetic acid tert-butyl ester (5292-43-3) → <1R,1α(S*),3α(E)>-1-Cyano-1-(3-phenoxyphenyl)methyl 2,2-Dimethyl-3-<3-tert-butoxy-2-(tert-butylsulfonyl)-3-oxo-1-propenyl>cyclopropanecarboxylate (130051-21-7)

Guidance literature:

Multi-step reaction with 4 steps

1: 98 percent / t-BuOK / tetrahydrofuran / 1 h / Ambient temperature

2: 91 percent / Oxone / methanol; H₂O / Ambient temperature

3: 1) NaH / 1) THF, rt, DMF, 2) 4 d, rt

4: 74 percent / DMAP, dicyclohexylcarbodiimide / CH₂Cl₂ / 18 h / Ambient temperature

With dmap; Oxone; potassium tert-butylate; sodium hydride; dicyclohexyl-carbodiimide; In tetrahydrofuran; methanol; dichloromethane; water;

DOI:10.1021/jo00028a034

Reference yield:

(1R)-cis-hemicaronaldehydic acid (28075-68-5) → <1R,1α(S*),3α(E)>-1-Cyano-1-(3-phenoxyphenyl)methyl 2,2-Dimethyl-3-<3-tert-butoxy-2-(tert-butylsulfonyl)-3-oxo-1-propenyl>cyclopropanecarboxylate (130051-21-7)

Guidance literature:

Multi-step reaction with 2 steps

1: 1) NaH / 1) THF, rt, DMF, 2) 4 d, rt

2: 74 percent / DMAP, dicyclohexylcarbodiimide / CH₂Cl₂ / 18 h / Ambient temperature

With dmap; sodium hydride; dicyclohexyl-carbodiimide; In dichloromethane;

DOI:10.1021/jo00028a034

upstream raw materials:

(1R,1α,3α)-6,6-Dimethyl-4-<2-tert-butoxy-2-oxo-1-(tert-butylsulfonyl)ethyl>-3-oxabicyclo<3.1.0>hexan-2-one

(S)-m-phenoxybenzaldehyde cyanohydrin

bromoacetic acid tert-butyl ester

(1R)-cis-hemicaronaldehydic acid

Downstream raw materials:

(1R,3S)-3-((Z)-2-tert-Butoxycarbonyl-vinyl)-2,2-dimethyl-cyclopropanecarboxylic acid (S)-cyano-(3-phenoxy-phenyl)-methyl ester

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