(3R,4S,5R)-5-((Z)-1-Carboxy-2-fluoro-vinyloxy)-4-hydroxy-3-phosphonooxy-cyclohex-1-enecarboxylic acid

Base Information

Chemical Name:(3R,4S,5R)-5-((Z)-1-Carboxy-2-fluoro-vinyloxy)-4-hydroxy-3-phosphonooxy-cyclohex-1-enecarboxylic acid
CAS No.:139704-83-9
Molecular Formula:C₁₀H₁₂FO₁₀P
Molecular Weight:342.171
Hs Code.:

Synonyms:(3R,4S,5R)-5-((Z)-1-Carboxy-2-fluoro-vinyloxy)-4-hydroxy-3-phosphonooxy-cyclohex-1-enecarboxylic acid

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Chemical Property of (3R,4S,5R)-5-((Z)-1-Carboxy-2-fluoro-vinyloxy)-4-hydroxy-3-phosphonooxy-cyclohex-1-enecarboxylic acid

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Technology Process of (3R,4S,5R)-5-((Z)-1-Carboxy-2-fluoro-vinyloxy)-4-hydroxy-3-phosphonooxy-cyclohex-1-enecarboxylic acid

There total 5 articles about (3R,4S,5R)-5-((Z)-1-Carboxy-2-fluoro-vinyloxy)-4-hydroxy-3-phosphonooxy-cyclohex-1-enecarboxylic acid 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:

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

: 139704-83-9
(3R,4S,5R)-5-((Z)-1-Carboxy-2-fluoro-vinyloxy)-4-hydroxy-3-phosphonooxy-cyclohex-1-enecarboxylic acid

Guidance literature:: Multi-step reaction with 5 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

5: 1.) bromotrimethylsilane, pyridine, 2.) D₂O, 3.) 1 N NaOH in D₂O

With pyridine; 1H-tetrazole; sodium hydroxide; trimethylsilyl bromide; Dowex 50W-X₈ resin (H⁺ form); water-d2; toluene-4-sulfonic acid; 3-chloro-benzenecarboperoxoic acid; sodium t-butanolate; In methanol; benzene;

Reference yield:

: 2-Difluoromethyl-2-((1R,5R,6R)-5,6-dihydroxy-3-methoxycarbonyl-cyclohex-3-enyloxy)-malonic acid dimethyl ester

: 139704-83-9
(3R,4S,5R)-5-((Z)-1-Carboxy-2-fluoro-vinyloxy)-4-hydroxy-3-phosphonooxy-cyclohex-1-enecarboxylic acid

Guidance literature:: Multi-step reaction with 3 steps

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

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

3: 1.) bromotrimethylsilane, pyridine, 2.) D₂O, 3.) 1 N NaOH in D₂O

With pyridine; 1H-tetrazole; sodium hydroxide; trimethylsilyl bromide; water-d2; toluene-4-sulfonic acid; 3-chloro-benzenecarboperoxoic acid; In benzene;

Reference yield:

: 139704-84-0
methyl <(1R),1α,5β,6α>-5-<2-bis(methoxycarbonyl)-1,1-difluoroethoxy>-8,8-dimethyl-7,9-dioxabicyclo<4.3.0>non-2-ene-3-carboxylate

: 139704-83-9
(3R,4S,5R)-5-((Z)-1-Carboxy-2-fluoro-vinyloxy)-4-hydroxy-3-phosphonooxy-cyclohex-1-enecarboxylic acid

Guidance literature:: Multi-step reaction with 4 steps

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

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

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

4: 1.) bromotrimethylsilane, pyridine, 2.) D₂O, 3.) 1 N NaOH in D₂O

With pyridine; 1H-tetrazole; sodium hydroxide; trimethylsilyl bromide; Dowex 50W-X₈ resin (H⁺ form); water-d2; toluene-4-sulfonic acid; 3-chloro-benzenecarboperoxoic acid; In methanol; benzene;