(3S,5R)-3-Hydroxy-5-methanesulfonyloxy-cyclohex-1-enecarboxylic acid methyl ester

Base Information

Chemical Name:(3S,5R)-3-Hydroxy-5-methanesulfonyloxy-cyclohex-1-enecarboxylic acid methyl ester
CAS No.:119999-61-0
Molecular Formula:C₉H₁₄O₆S
Molecular Weight:250.273
Hs Code.:

Synonyms:(3S,5R)-3-Hydroxy-5-methanesulfonyloxy-cyclohex-1-enecarboxylic acid methyl ester

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Chemical Property of (3S,5R)-3-Hydroxy-5-methanesulfonyloxy-cyclohex-1-enecarboxylic acid methyl ester

Chemical Property:

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Technology Process of (3S,5R)-3-Hydroxy-5-methanesulfonyloxy-cyclohex-1-enecarboxylic acid methyl ester

There total 8 articles about (3S,5R)-3-Hydroxy-5-methanesulfonyloxy-cyclohex-1-enecarboxylic acid methyl ester 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:

: 119999-60-9
(3S,5R)-3-Acetoxy-5-methanesulfonyloxy-cyclohex-1-enecarboxylic acid methyl ester

: 119999-61-0
(3S,5R)-3-Hydroxy-5-methanesulfonyloxy-cyclohex-1-enecarboxylic acid methyl ester

Guidance literature:: With sodium methylate; In methanol; at 0 - 5 ℃; for 0.666667h;
DOI:10.1021/ja00191a040

Reference yield:

: 76985-84-7
(-)-methyl (1β,2α,6β)-2-hydroxy-7-oxabicyclo<4,1,0>hept-3-ene-4-carboxylate

: 119999-61-0
(3S,5R)-3-Hydroxy-5-methanesulfonyloxy-cyclohex-1-enecarboxylic acid methyl ester

Guidance literature:: Multi-step reaction with 6 steps

1: 1.) PhSeH, n-BuLi; 2.) n-Bu₃SnH, AIBN / 1.) THF, hexane, -20 deg C, 2 h; 2.) benzene, reflux, 12 h

2: 58 percent / Ph₃P, diisopropyl azodicarboxylate / tetrahydrofuran / 30 h

3: 78 percent / NaOCH₃ / methanol / 5 h / 0 - 5 °C

4: Ph₃P, diisopropyl azodicarboxylate / tetrahydrofuran / 20 h / Ambient temperature

5: DMAP / CH₂Cl₂ / 4 h / Ambient temperature

6: NaOCH₃ / methanol / 0.67 h / 0 - 5 °C

With dmap; n-butyllithium; 2,2'-azobis(isobutyronitrile); di-isopropyl azodicarboxylate; tri-n-butyl-tin hydride; sodium methylate; Benzeneselenol; triphenylphosphine; In tetrahydrofuran; methanol; dichloromethane;
DOI:10.1021/ja00191a040

Reference yield:

: 119999-53-0
(-)-Methyl (3β,5α)-3-acetoxy-5-hydroxy-1-cyclohexene-1-carboxylate

: 119999-61-0
(3S,5R)-3-Hydroxy-5-methanesulfonyloxy-cyclohex-1-enecarboxylic acid methyl ester

Guidance literature:: Multi-step reaction with 2 steps

1: DMAP / CH₂Cl₂ / 4 h / Ambient temperature

2: NaOCH₃ / methanol / 0.67 h / 0 - 5 °C

With dmap; sodium methylate; In methanol; dichloromethane;
DOI:10.1021/ja00191a040