(3S,5R)-3,5-Dihydroxycyclohex-1-ene-1-carboxylic acid

Base Information

Chemical Name:(3S,5R)-3,5-Dihydroxycyclohex-1-ene-1-carboxylic acid
CAS No.:232952-09-9
Molecular Formula:C7H10 O4
Molecular Weight:158.15
Hs Code.:
DSSTox Substance ID:DTXSID20442983
Nikkaji Number:J1.100.995F
Wikidata:Q82260631
Mol file:232952-09-9.mol

Synonyms:232952-09-9;4-Deoxyshikimic acid;(3S,5R)-3,5-Dihydroxycyclohex-1-ene-1-carboxylic acid;SCHEMBL14448597;DTXSID20442983;1-Cyclohexene-1-carboxylicacid,3,5-dihydroxy-,(3S,5R)-(9ci)

Suppliers and Price of (3S,5R)-3,5-Dihydroxycyclohex-1-ene-1-carboxylic acid

Supply Marketing:

Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

Manufacturers and distributors:

Manufacture/Brand
Chemicals and raw materials
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price

Total 1 raw suppliers

Chemical Property of (3S,5R)-3,5-Dihydroxycyclohex-1-ene-1-carboxylic acid

Chemical Property:

PSA：77.76000
LogP:-0.48700
XLogP3:-0.7
Hydrogen Bond Donor Count:3
Hydrogen Bond Acceptor Count:4
Rotatable Bond Count:1
Exact Mass:158.05790880
Heavy Atom Count:11
Complexity:197

Purity/Quality:

Safty Information:

Pictogram(s):
Hazard Codes:

MSDS Files:: SDS file from LookChem

Useful:

Canonical SMILES:C1C(CC(=CC1O)C(=O)O)O
Isomeric SMILES:C1[C@@H](CC(=C[C@H]1O)C(=O)O)O

Technology Process of (3S,5R)-3,5-Dihydroxycyclohex-1-ene-1-carboxylic acid

There total 7 articles about (3S,5R)-3,5-Dihydroxycyclohex-1-ene-1-carboxylic 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: 99.0%

: 232952-15-7
(3S,5S)-3,5-bis(tert-butyldimethylsilyloxy)cyclohex-1-enecarboxylic acid

: 232952-09-9,232952-17-9
4-deoxyshikimic acid

Guidance literature:: With hydrogenchloride; In ethanol; at 0 - 20 ℃; for 2h;

Reference yield:

: 40983-58-2
methyl shikimate

: 232952-09-9,232952-17-9
4-deoxyshikimic acid

Guidance literature:: Multi-step reaction with 7 steps

1: 87 percent / Et₃N, DMAP, Bu₄NI / dimethylformamide / 1.) 0 deg C, 1 h, 2.) r.t., 3 h

2: 82 percent / DMAP / acetonitrile / 24 h / Ambient temperature

3: 93 percent / DIBAL-H / toluene / 0.25 h / -78 °C

4: 62 percent / Bu₃SnH, AIBN / toluene / 1 h / Heating

5: 83 percent / PDC, molecular sieves 4 Angstroem / CH₂Cl₂ / 2 h / Ambient temperature

6: 98 percent / NaH₂PO₄, NaClO₂, H₂O, 2-methylbut-2-ene / tetrahydrofuran; 2-methyl-propan-2-ol / 18 h / Ambient temperature

7: 99 percent / HCl / ethanol / 2 h / 0 - 20 °C

With hydrogenchloride; dmap; sodium chlorite; sodium dihydrogenphosphate; dipyridinium dichromate; 2-methyl-but-2-ene; 2,2'-azobis(isobutyronitrile); 4 A molecular sieve; water; tri-n-butyl-tin hydride; tetra-(n-butyl)ammonium iodide; diisobutylaluminium hydride; triethylamine; In tetrahydrofuran; ethanol; dichloromethane; N,N-dimethyl-formamide; toluene; acetonitrile; tert-butyl alcohol;

Reference yield:

: 101906-40-5
methyl (3S,4S,5S)-3,5-bis(tert-butyldimethylsilyloxy)-4-phenoxythiocarbonyloxycyclohex-1-enecarboxylate

: 232952-09-9,232952-17-9
4-deoxyshikimic acid

Guidance literature:: Multi-step reaction with 5 steps

1: 93 percent / DIBAL-H / toluene / 0.25 h / -78 °C

2: 62 percent / Bu₃SnH, AIBN / toluene / 1 h / Heating

3: 83 percent / PDC, molecular sieves 4 Angstroem / CH₂Cl₂ / 2 h / Ambient temperature

4: 98 percent / NaH₂PO₄, NaClO₂, H₂O, 2-methylbut-2-ene / tetrahydrofuran; 2-methyl-propan-2-ol / 18 h / Ambient temperature

5: 99 percent / HCl / ethanol / 2 h / 0 - 20 °C

With hydrogenchloride; sodium chlorite; sodium dihydrogenphosphate; dipyridinium dichromate; 2-methyl-but-2-ene; 2,2'-azobis(isobutyronitrile); 4 A molecular sieve; water; tri-n-butyl-tin hydride; diisobutylaluminium hydride; In tetrahydrofuran; ethanol; dichloromethane; toluene; tert-butyl alcohol;