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

Base Information

• Chemical Name: (1R,4S,5R,6S)-4,5,6-Trimethoxy-cyclohex-2-enol
• CAS No.: 135456-81-4
• Molecular Formula: C₉H₁₆O₄
• Molecular Weight: 188.224
• Mol file: 135456-81-4.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 8 articles about (1R,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: 86.0%

(Z)-(2R,3R,4S)-2,3,4-Trimethoxy-6-trimethylsilanyl-hex-5-enal (135456-80-3) → (1R,4S,5R,6S)-4,5,6-Trimethoxy-cyclohex-2-enol (135456-81-4)

Guidance literature:

With boron trifluoride diethyl etherate; In dichloromethane; Ambient temperature;

DOI:10.1021/jo00017a005

Reference yield:

O2,O3,O4-trimethyl-L-arabinose diethyl dithioacetal (135456-73-4) → (1R,4S,5R,6S)-4,5,6-Trimethoxy-cyclohex-2-enol (135456-81-4)

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: 86 percent / BF₃*Et₂O / CH₂Cl₂ / Ambient temperature

With 1H-imidazole; dmap; n-butyllithium; oxalyl dichloride; N,N,N,N,-tetramethylethylenediamine; boron trifluoride diethyl etherate; potassium tert-butylate; hydrogen; 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:

tert-Butyl-((2S,3R,4S)-6,6-dibromo-2,3,4-trimethoxy-hex-5-enyloxy)-dimethyl-silane (135456-76-7) → (1R,4S,5R,6S)-4,5,6-Trimethoxy-cyclohex-2-enol (135456-81-4)

Guidance literature:

Multi-step reaction with 5 steps

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

2: 91 percent / H₂ / Pd/BaSO₄ / pyridine / 20 h / Ambient temperature

3: 80 percent / HOAc / H₂O / 16 h / Ambient temperature

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

5: 86 percent / BF₃*Et₂O / CH₂Cl₂ / Ambient temperature

With n-butyllithium; oxalyl dichloride; N,N,N,N,-tetramethylethylenediamine; boron trifluoride diethyl etherate; hydrogen; acetic acid; dimethyl sulfoxide; triethylamine; Pd-BaSO₄; In pyridine; dichloromethane; water;

DOI:10.1021/jo00017a005

upstream raw materials:

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

O²,O³,O⁴-trimethyl-L-arabinose diethyl dithioacetal

(Z)-(2S,3R,4S)-2,3,4-Trimethoxy-6-trimethylsilanyl-hex-5-en-1-ol

(2R,3S,4S)-5-(tert-Butyl-dimethyl-silanyloxy)-2,3,4-trimethoxy-pentanal

Downstream raw materials:

3α,4β,5β,6α-tetramethoxycyclohex-4-ene-1α,2α-diol