(2Z)-(1R,3S,4R,5S)-2-cyanomethylene-1,3-dihydroxy-4,5-dimethoxycyclohexane

Base Information

Chemical Name:(2Z)-(1R,3S,4R,5S)-2-cyanomethylene-1,3-dihydroxy-4,5-dimethoxycyclohexane
CAS No.:142631-54-7
Molecular Formula:C₁₀H₁₅NO₄
Molecular Weight:213.233
Hs Code.:

Synonyms:(2Z)-(1R,3S,4R,5S)-2-cyanomethylene-1,3-dihydroxy-4,5-dimethoxycyclohexane

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Chemical Property of (2Z)-(1R,3S,4R,5S)-2-cyanomethylene-1,3-dihydroxy-4,5-dimethoxycyclohexane

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Technology Process of (2Z)-(1R,3S,4R,5S)-2-cyanomethylene-1,3-dihydroxy-4,5-dimethoxycyclohexane

There total 14 articles about (2Z)-(1R,3S,4R,5S)-2-cyanomethylene-1,3-dihydroxy-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: 80.0%

: 142631-53-6
(2E)-(1R,3S,4R,5S)-2-cyanomethylene-3-hydroxy-4,5-dimethoxy-1-(p-methoxybenzoyloxy)cyclohexane

: 142631-54-7
(2Z)-(1R,3S,4R,5S)-2-cyanomethylene-1,3-dihydroxy-4,5-dimethoxycyclohexane

Guidance literature:: With water; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In dichloromethane; for 32h; Ambient temperature;

Reference yield:

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

: 142631-54-7
(2Z)-(1R,3S,4R,5S)-2-cyanomethylene-1,3-dihydroxy-4,5-dimethoxycyclohexane

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: 37 percent / KOtBu / toluene / 6 h / Ambient temperature

13: 71 percent / pyridinium toluene-p-sulfonate / ethanol / 25 h / 50 °C

14: 80 percent / DDQ, H₂O / CH₂Cl₂ / 32 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:

: 142543-92-8
1L-1,2-O-isopropylidene-5,6-di-O-methyl-chiro-inositol

: 142631-54-7
(2Z)-(1R,3S,4R,5S)-2-cyanomethylene-1,3-dihydroxy-4,5-dimethoxycyclohexane

Guidance literature:: Multi-step reaction with 12 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: 37 percent / KOtBu / toluene / 6 h / Ambient temperature

11: 71 percent / pyridinium toluene-p-sulfonate / ethanol / 25 h / 50 °C

12: 80 percent / DDQ, H₂O / CH₂Cl₂ / 32 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;