ethyl 2-acetoxy-3,4-dihydroxy-6-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]-(1S,2S,3S,4S,6R)-cyclohexane-1-carboxylate

Base Information

Chemical Name:ethyl 2-acetoxy-3,4-dihydroxy-6-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]-(1S,2S,3S,4S,6R)-cyclohexane-1-carboxylate
CAS No.:331005-79-9
Molecular Formula:C₁₆H₂₆O₈
Molecular Weight:346.378
Hs Code.:

Synonyms:ethyl 2-acetoxy-3,4-dihydroxy-6-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]-(1S,2S,3S,4S,6R)-cyclohexane-1-carboxylate

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Chemical Property of ethyl 2-acetoxy-3,4-dihydroxy-6-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]-(1S,2S,3S,4S,6R)-cyclohexane-1-carboxylate

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Technology Process of ethyl 2-acetoxy-3,4-dihydroxy-6-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]-(1S,2S,3S,4S,6R)-cyclohexane-1-carboxylate

There total 7 articles about ethyl 2-acetoxy-3,4-dihydroxy-6-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]-(1S,2S,3S,4S,6R)-cyclohexane-1-carboxylate 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: 88.0%

: 331005-76-6
ethyl 2-acetoxy-6-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]-(1S,2R,6R)-3-cyclohexene-1-carboxylate

: 331005-79-9
ethyl 2-acetoxy-3,4-dihydroxy-6-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]-(1S,2S,3S,4S,6R)-cyclohexane-1-carboxylate

Guidance literature:: With osmium(VIII) oxide; N-methyl-2-indolinone; In acetone; toluene; at 20 ℃; for 12h;
DOI:10.1016/S0957-4166(00)00429-8

Reference yield:

: 91926-90-8,917877-01-1
ethyl (Z)-3-((S)-2,2-dimethyl-1,3-dioxolan-4-yl)acrylate

: 331005-79-9
ethyl 2-acetoxy-3,4-dihydroxy-6-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]-(1S,2S,3S,4S,6R)-cyclohexane-1-carboxylate

Guidance literature:: Multi-step reaction with 6 steps

1: DIBAL-H / CH₂Cl₂

2: 65 percent / PDC / CH₂Cl₂ / 2 h / Heating

3: 68 percent / NaH; H₂ / tetrahydrofuran / 0.25 h / 50 °C

4: 33.4 percent / CeCl₃*7H₂O; NaBH₄ / ethanol / 1 h / 20 °C

5: 100 percent / pyridine; DMAP / 1 h / 20 °C

6: 88 percent / aq. NMO; OsO₄ / acetone; toluene / 12 h / 20 °C

With pyridine; dmap; sodium tetrahydroborate; osmium(VIII) oxide; dipyridinium dichromate; N-methyl-2-indolinone; cerium(III) chloride; hydrogen; sodium hydride; diisobutylaluminium hydride; In tetrahydrofuran; ethanol; dichloromethane; acetone; toluene; 3: Michael-Wittig reaction;
DOI:10.1016/S0957-4166(00)00429-8

Reference yield:

: 115509-80-3
cis-2,3-Didesoxy-4,5-O-isopropyliden-aldehydo-D-glycero-pent-2-enose

: 331005-79-9
ethyl 2-acetoxy-3,4-dihydroxy-6-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]-(1S,2S,3S,4S,6R)-cyclohexane-1-carboxylate

Guidance literature:: Multi-step reaction with 4 steps

1: 68 percent / NaH; H₂ / tetrahydrofuran / 0.25 h / 50 °C

2: 33.4 percent / CeCl₃*7H₂O; NaBH₄ / ethanol / 1 h / 20 °C

3: 100 percent / pyridine; DMAP / 1 h / 20 °C

4: 88 percent / aq. NMO; OsO₄ / acetone; toluene / 12 h / 20 °C

With pyridine; dmap; sodium tetrahydroborate; osmium(VIII) oxide; N-methyl-2-indolinone; cerium(III) chloride; hydrogen; sodium hydride; In tetrahydrofuran; ethanol; acetone; toluene; 1: Michael-Wittig reaction;
DOI:10.1016/S0957-4166(00)00429-8