(2E)-(1R,3S,4S,5S)-3-acetoxy-2-cyanomethylene-1-hydroxy-4,5-dimethoxycyclohexane

Base Information

• Chemical Name: (2E)-(1R,3S,4S,5S)-3-acetoxy-2-cyanomethylene-1-hydroxy-4,5-dimethoxycyclohexane
• CAS No.: 135131-70-3
• Molecular Formula: C₁₂H₁₇NO₅
• Molecular Weight: 255.271
• Mol file: 135131-70-3.mol

Synonyms:(2E)-(1R,3S,4S,5S)-3-acetoxy-2-cyanomethylene-1-hydroxy-4,5-dimethoxycyclohexane

Chemical Property of (2E)-(1R,3S,4S,5S)-3-acetoxy-2-cyanomethylene-1-hydroxy-4,5-dimethoxycyclohexane

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2E)-(1R,3S,4S,5S)-3-acetoxy-2-cyanomethylene-1-hydroxy-4,5-dimethoxycyclohexane

There total 15 articles about (2E)-(1R,3S,4S,5S)-3-acetoxy-2-cyanomethylene-1-hydroxy-4,5-dimethoxycyclohexane 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: 72.0%

(2E)-(1R,3S,4S,5S)-3-acetoxy-2-cyanomethylene-4,5-dimethoxy-1-(p-methoxybenzoyloxy)cyclohexane (135131-69-0) → (2E)-(1R,3S,4S,5S)-3-acetoxy-2-cyanomethylene-1-hydroxy-4,5-dimethoxycyclohexane (135131-70-3)

Guidance literature:

With water; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In dichloromethane; for 18h; Ambient temperature;

Reference yield:

1L-3,4,:5,6-di-O-isopropylidene-2-O-methyl-chiro-inositol (58769-23-6) → (2E)-(1R,3S,4S,5S)-3-acetoxy-2-cyanomethylene-1-hydroxy-4,5-dimethoxycyclohexane (135131-70-3)

Guidance literature:

Multi-step reaction with 15 steps

1: 1) NaH / 1) DMF, 0 deg C, 40 min, 2) r.t., 30 min

2: 81 percent / pTsOH*H₂O / methanol / 7 h / 0 °C

3: 1) pyridine, 2) pyridine / 1) 0 deg C, 27 h, 2) r.t., 6 h

4: 84 percent / NaOMe / methanol / 3 h / Ambient temperature

5: 91 percent / LiAlH₄ / tetrahydrofuran / 3 h / Ambient temperature

6: 1) NaH / 1) DMF, 0 deg C, 45 min, 2) r.t., 12 h

7: 92 percent / pTsOH / methanol / 4 h / Ambient temperature

8: 87 percent / pyridine / 13 h / 70 °C

9: 98 percent / pTsOH / CH₂Cl₂ / 0.5 h / Ambient temperature

10: 89 percent / NaOMe / methanol / 9 h / 50 °C

11: 87 percent / PCC, molecular sieves / CH₂Cl₂ / 6 h / Ambient temperature

12: 43 percent / KOtBu / toluene / 6 h / Ambient temperature

13: 97 percent / pyridinium toluene-p-sulfonate / ethanol / 4 h / 50 °C

14: 100 percent / pyridine / 2 h / Ambient temperature

15: 72 percent / DDQ, H₂O / CH₂Cl₂ / 18 h / Ambient temperature

With pyridine; lithium aluminium tetrahydride; molecular sieve; potassium tert-butylate; water; sodium methylate; pyridinium p-toluenesulfonate; sodium hydride; toluene-4-sulfonic acid; pyridinium chlorochromate; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In tetrahydrofuran; methanol; ethanol; dichloromethane; toluene;

Reference yield:

1L-1,2-O-isopropylidene-5,6-di-O-methyl-chiro-inositol (142543-92-8) → (2E)-(1R,3S,4S,5S)-3-acetoxy-2-cyanomethylene-1-hydroxy-4,5-dimethoxycyclohexane (135131-70-3)

Guidance literature:

Multi-step reaction with 13 steps

1: 1) pyridine, 2) pyridine / 1) 0 deg C, 27 h, 2) r.t., 6 h

2: 84 percent / NaOMe / methanol / 3 h / Ambient temperature

3: 91 percent / LiAlH₄ / tetrahydrofuran / 3 h / Ambient temperature

4: 1) NaH / 1) DMF, 0 deg C, 45 min, 2) r.t., 12 h

5: 92 percent / pTsOH / methanol / 4 h / Ambient temperature

6: 87 percent / pyridine / 13 h / 70 °C

7: 98 percent / pTsOH / CH₂Cl₂ / 0.5 h / Ambient temperature

8: 89 percent / NaOMe / methanol / 9 h / 50 °C

9: 87 percent / PCC, molecular sieves / CH₂Cl₂ / 6 h / Ambient temperature

10: 43 percent / KOtBu / toluene / 6 h / Ambient temperature

11: 97 percent / pyridinium toluene-p-sulfonate / ethanol / 4 h / 50 °C

12: 100 percent / pyridine / 2 h / Ambient temperature

13: 72 percent / DDQ, H₂O / CH₂Cl₂ / 18 h / Ambient temperature

With pyridine; lithium aluminium tetrahydride; molecular sieve; potassium tert-butylate; water; sodium methylate; pyridinium p-toluenesulfonate; sodium hydride; toluene-4-sulfonic acid; pyridinium chlorochromate; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In tetrahydrofuran; methanol; ethanol; dichloromethane; toluene;

upstream raw materials:

(2E)-(1R,3S,4S,5S)-3-acetoxy-2-cyanomethylene-4,5-dimethoxy-1-(p-methoxybenzoyloxy)cyclohexane

1L-3,4,:5,6-di-O-isopropylidene-2-O-methyl-chiro-inositol

1D-(1,2,5/3,4)-3,4-O-isopropylidene-1,2-di-O-methylcyclohexanepentaol

1L-1,2-O-isopropylidene-5,6-di-O-methyl-chiro-inositol

Downstream raw materials:

simmondsin penta-O-acetate

(7Z)-(1R,3S,4R,5S)-2-(cyanomethylene)-3-hydroxy-4,5-dimethoxycyclohexyl β-D-glucopyranoside

Refernces

• 1、 Chida, Noritaka,Yamada, Ken,Ogawa, Seiichiro. "Total Synthesis of Simmondsin". . p. 588 - 590. Retrieved 2007/10/02.