(1S,4S,5R,6S)-4,5,6-Trimethoxy-cyclohex-2-enol

Base Information

Chemical Name:(1S,4S,5R,6S)-4,5,6-Trimethoxy-cyclohex-2-enol
CAS No.:135557-45-8
Molecular Formula:C₉H₁₆O₄
Molecular Weight:188.224
Hs Code.:

Synonyms:(1S,4S,5R,6S)-4,5,6-Trimethoxy-cyclohex-2-enol

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Chemical Property of (1S,4S,5R,6S)-4,5,6-Trimethoxy-cyclohex-2-enol

Chemical Property:

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Technology Process of (1S,4S,5R,6S)-4,5,6-Trimethoxy-cyclohex-2-enol

There total 8 articles about (1S,4S,5R,6S)-4,5,6-Trimethoxy-cyclohex-2-enol 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: 68.0%

: 135456-80-3
(Z)-(2R,3R,4S)-2,3,4-Trimethoxy-6-trimethylsilanyl-hex-5-enal

: 135557-45-8
(1S,4S,5R,6S)-4,5,6-Trimethoxy-cyclohex-2-enol

Guidance literature:: With tin(IV) chloride; In dichloromethane; -78 deg C -> room temp.;
DOI:10.1021/jo00017a005

Reference yield:

: 135456-73-4
O²,O³,O⁴-trimethyl-L-arabinose diethyl dithioacetal

: 135557-45-8
(1S,4S,5R,6S)-4,5,6-Trimethoxy-cyclohex-2-enol

Guidance literature:: Multi-step reaction with 8 steps

1: 86 percent / imidazole, DMAP / dimethylformamide / 12 h / Ambient temperature

2: 98 percent / HgO, HgCl₂ / acetone; H₂O / 1 h / 50 - 55 °C

3: 81 percent / KOtBu, PPh₃ / toluene / -20 deg C -> room temp.

4: 1) n-BuLi, TMEDA / 1) THF, -78 deg C, 2) -78 deg C -> room temp.

5: 91 percent / H₂ / Pd/BaSO₄ / pyridine / 20 h / Ambient temperature

6: 80 percent / HOAc / H₂O / 16 h / Ambient temperature

7: 1) (COCl)2, DMSO, 2) Et₃N / 1) CH₂Cl₂, -78 deg C, 2) up to 0 deg C

8: 68 percent / SnCl₄ / CH₂Cl₂ / -78 deg C -> room temp.

With 1H-imidazole; dmap; n-butyllithium; oxalyl dichloride; N,N,N,N,-tetramethylethylenediamine; potassium tert-butylate; hydrogen; tin(IV) chloride; acetic acid; dimethyl sulfoxide; triethylamine; triphenylphosphine; mercury dichloride; mercury(II) oxide; Pd-BaSO₄; In pyridine; dichloromethane; water; N,N-dimethyl-formamide; acetone; toluene;
DOI:10.1021/jo00017a005

Reference yield:

: 135456-74-5
((2S,3S,4R)-5,5-Bis-ethylsulfanyl-2,3,4-trimethoxy-pentyloxy)-tert-butyl-dimethyl-silane

: 135557-45-8
(1S,4S,5R,6S)-4,5,6-Trimethoxy-cyclohex-2-enol

Guidance literature:: Multi-step reaction with 7 steps

1: 98 percent / HgO, HgCl₂ / acetone; H₂O / 1 h / 50 - 55 °C

2: 81 percent / KOtBu, PPh₃ / toluene / -20 deg C -> room temp.

3: 1) n-BuLi, TMEDA / 1) THF, -78 deg C, 2) -78 deg C -> room temp.

4: 91 percent / H₂ / Pd/BaSO₄ / pyridine / 20 h / Ambient temperature

5: 80 percent / HOAc / H₂O / 16 h / Ambient temperature

6: 1) (COCl)2, DMSO, 2) Et₃N / 1) CH₂Cl₂, -78 deg C, 2) up to 0 deg C

7: 68 percent / SnCl₄ / CH₂Cl₂ / -78 deg C -> room temp.

With n-butyllithium; oxalyl dichloride; N,N,N,N,-tetramethylethylenediamine; potassium tert-butylate; hydrogen; tin(IV) chloride; acetic acid; dimethyl sulfoxide; triethylamine; triphenylphosphine; mercury dichloride; mercury(II) oxide; Pd-BaSO₄; In pyridine; dichloromethane; water; acetone; toluene;
DOI:10.1021/jo00017a005