methyl <(1R),1α,5β,6α>-5--8,8-dimethyl-7,9-dioxabicyclo<4.3.0>non-2-ene-3-carboxylate

Base Information

Chemical Name:methyl <(1R),1α,5β,6α>-5--8,8-dimethyl-7,9-dioxabicyclo<4.3.0>non-2-ene-3-carboxylate
CAS No.:96283-92-0
Molecular Formula:C₁₆H₂₂O₉
Molecular Weight:358.345
Hs Code.:

methyl <(1R),1α,5β,6α>-5-<bis(methoxycarbonyl)methoxy>-8,8-dimethyl-7,9-dioxabicyclo<4.3.0>non-2-ene-3-carboxylate

Synonyms:methyl <(1R),1α,5β,6α>-5--8,8-dimethyl-7,9-dioxabicyclo<4.3.0>non-2-ene-3-carboxylate

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Chemical Property of methyl <(1R),1α,5β,6α>-5--8,8-dimethyl-7,9-dioxabicyclo<4.3.0>non-2-ene-3-carboxylate

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Technology Process of methyl <(1R),1α,5β,6α>-5--8,8-dimethyl-7,9-dioxabicyclo<4.3.0>non-2-ene-3-carboxylate

There total 1 articles about methyl <(1R),1α,5β,6α>-5--8,8-dimethyl-7,9-dioxabicyclo<4.3.0>non-2-ene-3-carboxylate 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: 85.0%

: 88165-26-8
methyl 3,4-O-isopropylideneshikimate

: 6773-29-1
dimethyl diazomalonate

: 96283-92-0
methyl <(1R),1α,5β,6α>-5--8,8-dimethyl-7,9-dioxabicyclo<4.3.0>non-2-ene-3-carboxylate

Guidance literature:: dirhodium tetraacetate; In benzene; Heating;
DOI:10.1016/S0040-4039(00)98455-7

Reference yield:

: 96283-92-0
methyl <(1R),1α,5β,6α>-5--8,8-dimethyl-7,9-dioxabicyclo<4.3.0>non-2-ene-3-carboxylate

: 89771-75-5,27840-48-8
5-enol-pyruvoylshikimate 3-phosphate (EPSP)

Guidance literature:: Multi-step reaction with 8 steps

1: Et₃N / CH₂Cl₂

2: CH₂Cl₂ / Ambient temperature

3: 83 percent / dimethylsulfoxide / 6 h / 95 °C

4: 90 percent / 80percent aqueous acetic acid / 3 h / 65 - 70 °C

5: NaOH / tetrahydrofuran; H₂O / 3 h / 0 °C

6: water-soluble carbodiimide, DMAP / tetrahydrofuran / 3 h / Ambient temperature

8: 1.) diazabicyclo<5.4.0>undec-7-ene, 2.) aqueous NaOH / 1.) C₅H₅N, rt, 72h, 2.) 5h, 0 deg C

With dmap; sodium hydroxide; acetic acid; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; In tetrahydrofuran; dichloromethane; water; dimethyl sulfoxide;
DOI:10.1016/S0040-4039(00)98455-7

Reference yield:

: 96283-92-0
methyl <(1R),1α,5β,6α>-5--8,8-dimethyl-7,9-dioxabicyclo<4.3.0>non-2-ene-3-carboxylate

: 139704-87-3,139891-16-0
dimethyl <(4aR),4aβ,8α,8aα>-2,3,4a,5,8,8a-hexahydro-2-oxo-3-(difluoromethyl)-8-<oxy>-1,4-benzodioxin-3,6-dicarboxylate

Guidance literature:: Multi-step reaction with 4 steps

1: 1.) sodium tert-butoxide / 1.) THF, RT, 30 min, 2.) HMPT, 45 deg C, 1 h

2: Dowex 50W-X₈ resin (H⁺ form) / methanol / 63 h / 60 - 65 °C

3: p-toluenesulfonic acid / benzene / 5.5 h / Heating

4: 1.) tetrazole, 2.) m-chloroperoxybenzoic acid (mCPBA) / 1.) THF, RT, 1.5 h, 2.) THF, CH₂Cl₂, from 0 deg C to RT, 40 min

With 1H-tetrazole; Dowex 50W-X₈ resin (H⁺ form); toluene-4-sulfonic acid; 3-chloro-benzenecarboperoxoic acid; sodium t-butanolate; In methanol; benzene;