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

Base Information Edit

Chemical Name:(2E)-(1R,3S,4S,5S)-3-acetoxy-2-cyanomethylene-4,5-dimethoxy-1-(p-methoxybenzoyloxy)cyclohexane
CAS No.:135131-69-0
Molecular Formula:C₂₀H₂₅NO₆
Molecular Weight:375.422
Hs Code.:
Mol file:135131-69-0.mol

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

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

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

There total 16 articles about (2E)-(1R,3S,4S,5S)-3-acetoxy-2-cyanomethylene-4,5-dimethoxy-1-(p-methoxybenzoyloxy)cyclohexane 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: 100.0%

: 108-24-7
acetic anhydride

: 142543-96-2
(2Z)-(1R,3S,4S,5S)-2-cyanomethylene-3-hydroxy-4,5-dimethoxy-1-(p-methoxybenzoyloxy)cyclohexane

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

Guidance literature:: With pyridine; for 2h; Ambient temperature;

Reference yield:

: 58769-23-6
1L-3,4,:5,6-di-O-isopropylidene-2-O-methyl-chiro-inositol

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

Guidance literature:: Multi-step reaction with 14 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

With pyridine; lithium aluminium tetrahydride; molecular sieve; potassium tert-butylate; sodium methylate; pyridinium p-toluenesulfonate; sodium hydride; toluene-4-sulfonic acid; pyridinium chlorochromate; In tetrahydrofuran; methanol; ethanol; dichloromethane; toluene;

Reference yield:

: 135131-63-4
1D-(1,2,5/3,4)-3,4-O-isopropylidene-1,2-di-O-methylcyclohexanepentaol

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

Guidance literature:: Multi-step reaction with 9 steps

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

2: 92 percent / pTsOH / methanol / 4 h / Ambient temperature

3: 87 percent / pyridine / 13 h / 70 °C

4: 98 percent / pTsOH / CH₂Cl₂ / 0.5 h / Ambient temperature

5: 89 percent / NaOMe / methanol / 9 h / 50 °C

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

7: 43 percent / KOtBu / toluene / 6 h / Ambient temperature

8: 97 percent / pyridinium toluene-p-sulfonate / ethanol / 4 h / 50 °C

9: 100 percent / pyridine / 2 h / Ambient temperature

With pyridine; molecular sieve; potassium tert-butylate; sodium methylate; pyridinium p-toluenesulfonate; sodium hydride; toluene-4-sulfonic acid; pyridinium chlorochromate; In methanol; ethanol; dichloromethane; toluene;