methyl N-[(1S,4S,5S,6R)-2-(1,3-benzodioxol-5-yl)-5,6-dihydroxycyclohex-3-en-1-yl]carbamate

Base Information

Chemical Name:methyl N-[(1S,4S,5S,6R)-2-(1,3-benzodioxol-5-yl)-5,6-dihydroxycyclohex-3-en-1-yl]carbamate
CAS No.:228245-40-7
Molecular Formula:C₁₅H₁₇NO₆
Molecular Weight:307.303
Hs Code.:

Synonyms:methyl N-[(1S,4S,5S,6R)-2-(1,3-benzodioxol-5-yl)-5,6-dihydroxycyclohex-3-en-1-yl]carbamate

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Chemical Property of methyl N-[(1S,4S,5S,6R)-2-(1,3-benzodioxol-5-yl)-5,6-dihydroxycyclohex-3-en-1-yl]carbamate

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Technology Process of methyl N-[(1S,4S,5S,6R)-2-(1,3-benzodioxol-5-yl)-5,6-dihydroxycyclohex-3-en-1-yl]carbamate

There total 20 articles about methyl N-[(1S,4S,5S,6R)-2-(1,3-benzodioxol-5-yl)-5,6-dihydroxycyclohex-3-en-1-yl]carbamate 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: 95.0%

: 460731-79-7
6-aminocarbomethoxy-1,2-dihydroxy-5-(7-methoxybenzo[d][1,3]dioxol-5-yl)-4-cyclohexene-1-yl benzoate

: 228245-40-7
methyl N-[(1S,4S,5S,6R)-2-(1,3-benzodioxol-5-yl)-5,6-dihydroxycyclohex-3-en-1-yl]carbamate

Guidance literature:: With Dowex-50W; In methanol; at 20 ℃; for 20h;
DOI:10.1021/jo020129m

Reference yield: 95.0%

: 460731-70-8
methyl N-[(1S,4S,5S,6R)-2-(1,3-benzodioxol-5-yl)-5,6-(isopropylidenedioxy)cyclohex-3-en-1-yl]carbamate

: 228245-40-7
methyl N-[(1S,4S,5S,6R)-2-(1,3-benzodioxol-5-yl)-5,6-dihydroxycyclohex-3-en-1-yl]carbamate

Guidance literature:: With Dowex-50W; In methanol;
DOI:10.1016/S0040-4039(99)00434-7

Reference yield:

: 108-36-1
1,3-dibromobenzene

: 228245-40-7
methyl N-[(1S,4S,5S,6R)-2-(1,3-benzodioxol-5-yl)-5,6-dihydroxycyclohex-3-en-1-yl]carbamate

Guidance literature:: Multi-step reaction with 8 steps

1.1: Escherichia coli JM₁₀₉ (pDTG₆₀₁A)

2.1: p-toluenesulfonic acid

3.1: 1.3 g / NaIO₄ / methanol; various solvent(s) / 16 h / 20 °C

4.1: Pd(PPh₃)4; aq. Na₂CO₃ / benzene; ethanol / 8 h / Heating

4.2: 31 percent / Mo(CO)6 / benzene; ethanol / 12 h

5.1: cerium chloride / methanol / 0.08 h

5.2: 50 percent / NaBH₄ / methanol / 0.5 h / 0 °C

6.1: 52 percent / tributylphosphine; DEAD / tetrahydrofuran / 2 h / 25 °C

7.1: Dowex 50 x 8-100 ion-exchange resin / methanol / 12 h / 20 °C

8.1: 95 percent / Dowex-50W / methanol / 20 h / 20 °C

With sodium periodate; tetrakis(triphenylphosphine) palladium⁽⁰⁾; cerium(III) chloride; tributylphosphine; Dowex 50 x 8-100 ion-exchange resin; Dowex-50W; Escherichia coli JM₁₀₉ (pDTG₆₀₁A); sodium carbonate; toluene-4-sulfonic acid; diethylazodicarboxylate; In tetrahydrofuran; methanol; ethanol; benzene;
DOI:10.1021/jo020129m