(1R,2R,3S,4S)-<3--2-bornyl>-(5R)-2-oxo-5-isopropylcyclohexenecarboxylate

Base Information

• Chemical Name: (1R,2R,3S,4S)-<3--2-bornyl>-(5R)-2-oxo-5-isopropylcyclohexenecarboxylate
• CAS No.: 170808-41-0
• Molecular Formula: C₃₄H₄₃NO₅S
• Molecular Weight: 577.785

Synonyms:(1R,2R,3S,4S)-<3--2-bornyl>-(5R)-2-oxo-5-isopropylcyclohexenecarboxylate

Chemical Property of (1R,2R,3S,4S)-<3--2-bornyl>-(5R)-2-oxo-5-isopropylcyclohexenecarboxylate

Chemical Property:

Purity/Quality:

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Technology Process of (1R,2R,3S,4S)-<3--2-bornyl>-(5R)-2-oxo-5-isopropylcyclohexenecarboxylate

There total 5 articles about (1R,2R,3S,4S)-<3--2-bornyl>-(5R)-2-oxo-5-isopropylcyclohexenecarboxylate 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: 70.0%

(1R,2R,3S,4S)-<3--2-bornyl>-(6RS)-6-(1,3-dioxolan-2-yl)-7-methyl-3-oxooctanoate → (1R,2R,3S,4S)-<3--2-bornyl>-(5S)-2-oxo-5-isopropylcyclohexenecarboxylate (171030-06-1) + (1R,2R,3S,4S)-<3--2-bornyl>-(5R)-2-oxo-5-isopropylcyclohexenecarboxylate (170808-41-0)

Guidance literature:

With acetic acid; In water; at 20 ℃; for 72h;

DOI:10.1016/0040-4039(95)01538-S

Reference yield:

3-methyl-2-methylene-butyraldehyde (4417-80-5) → (1R,2R,3S,4S)-<3--2-bornyl>-(5R)-2-oxo-5-isopropylcyclohexenecarboxylate (170808-41-0)

Guidance literature:

Multi-step reaction with 4 steps

1: 67 percent / HBr / 3.5 h / 5 - 20 °C

2: 1.) NaH, 2.) nBuLi

3: 74 percent / DMAP / toluene / 72 h / Heating

4: aq. AcOH / 72 h / Ambient temperature

With dmap; n-butyllithium; hydrogen bromide; sodium hydride; acetic acid; In toluene;

DOI:10.1016/0040-4020(95)00952-3

Reference yield:

2-[1-(bromomethyl)-2-methylpropyl]-1,3-dioxolane (173393-94-7) → (1R,2R,3S,4S)-<3--2-bornyl>-(5R)-2-oxo-5-isopropylcyclohexenecarboxylate (170808-41-0)

Guidance literature:

Multi-step reaction with 3 steps

1: 1.) NaH, 2.) nBuLi

2: 74 percent / DMAP / toluene / 72 h / Heating

3: aq. AcOH / 72 h / Ambient temperature

With dmap; n-butyllithium; sodium hydride; acetic acid; In toluene;

DOI:10.1016/0040-4020(95)00952-3

upstream raw materials:

3-methyl-2-methylene-butyraldehyde

2-[1-(bromomethyl)-2-methylpropyl]-1,3-dioxolane

methyl 6-(1,3-dioxolan-2-yl)-7-methyl-3-oxooctanoate

isovaleraldehyde

Downstream raw materials:

(1S,2S,3R)-2-(2,2-Dimethyl-[1,3]dioxan-5-ylidenemethyl)-3-isopropyl-6-oxo-cyclohexanecarboxylic acid (1R,2R,3S,4S)-3-[benzenesulfonyl-(3,5-dimethyl-phenyl)-amino]-1,7,7-trimethyl-bicyclo[2.2.1]hept-2-yl ester

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