Acetic acid (1R,2S,3S,4S,5R,6R)-2,3,4-triacetoxy-6-(7-methoxy-benzo[1,3]dioxol-5-yl)-5-methoxycarbonylamino-cyclohexyl ester

Base Information

• Chemical Name: Acetic acid (1R,2S,3S,4S,5R,6R)-2,3,4-triacetoxy-6-(7-methoxy-benzo[1,3]dioxol-5-yl)-5-methoxycarbonylamino-cyclohexyl ester
• CAS No.: 208193-12-8
• Molecular Formula: C₂₄H₂₉NO₁₃
• Molecular Weight: 539.493

Synonyms:Acetic acid (1R,2S,3S,4S,5R,6R)-2,3,4-triacetoxy-6-(7-methoxy-benzo[1,3]dioxol-5-yl)-5-methoxycarbonylamino-cyclohexyl ester

Chemical Property of Acetic acid (1R,2S,3S,4S,5R,6R)-2,3,4-triacetoxy-6-(7-methoxy-benzo[1,3]dioxol-5-yl)-5-methoxycarbonylamino-cyclohexyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Acetic acid (1R,2S,3S,4S,5R,6R)-2,3,4-triacetoxy-6-(7-methoxy-benzo[1,3]dioxol-5-yl)-5-methoxycarbonylamino-cyclohexyl ester

There total 19 articles about Acetic acid (1R,2S,3S,4S,5R,6R)-2,3,4-triacetoxy-6-(7-methoxy-benzo[1,3]dioxol-5-yl)-5-methoxycarbonylamino-cyclohexyl ester 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: 60.0%

acetic anhydride (108-24-7) + [(1R,2S,3S,4S,5R,6R)-2,3,4,5-Tetrahydroxy-6-(7-methoxy-benzo[1,3]dioxol-5-yl)-cyclohexyl]-carbamic acid methyl ester (208193-11-7) → Acetic acid (1R,2S,3S,4S,5R,6R)-2,3,4-triacetoxy-6-(7-methoxy-benzo[1,3]dioxol-5-yl)-5-methoxycarbonylamino-cyclohexyl ester (208193-12-8)

Guidance literature:

In pyridine; for 20h; Ambient temperature;

DOI:10.1016/S0040-4020(98)00975-2

Reference yield:

5-bromo-7-methoxy-1,3-benzodioxol (91511-83-0) → Acetic acid (1R,2S,3S,4S,5R,6R)-2,3,4-triacetoxy-6-(7-methoxy-benzo[1,3]dioxol-5-yl)-5-methoxycarbonylamino-cyclohexyl ester (208193-12-8)

Guidance literature:

Multi-step reaction with 18 steps

1: 1.) n-BuLi / 1.) THF, 2.) THF

2: POCl₃, DBU, pyridine

3: H₂ / Pd/C

4: H₃O⁽¹⁺⁾, MeOH

5: lithium (+)-bis(α-methylbenzyl)amide, LiCl / tetrahydrofuran / -78 °C

6: TMSN₃, (PhIO)n / CH₂Cl₂ / -15 °C

7: LiAlH₄ / diethyl ether

8: pyridine

9: imidazole / CH₂Cl₂

10: H₃O⁺

11: t-BuOK / hexamethylphosphoric acid triamide / 90 °C

12: Et₃N

14: H₂O₂, pyridine

15: H₂O₂, NaHCO₃ / methanol; tetrahydrofuran

16: L-selectride / tetrahydrofuran

17: aq. PhCO₂Na

18: pyridine

With pyridine; 1H-imidazole; methanol; sodium benzoate; lithium aluminium tetrahydride; n-butyllithium; trimethylsilylazide; (+)-bis(α-methylbenzyl)amine lithium salt; (PhIO)n; oxonium; potassium tert-butylate; hydrogen; dihydrogen peroxide; L-Selectride; sodium hydrogencarbonate; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; lithium chloride; trichlorophosphate; palladium on activated charcoal; In tetrahydrofuran; methanol; N,N,N,N,N,N-hexamethylphosphoric triamide; diethyl ether; dichloromethane;

DOI:10.1021/ja980407s

Reference yield:

6-(1,4-Dioxa-spiro[4.5]dec-7-en-8-yl)-4-methoxy-benzo[1,3]dioxole (208193-14-0) → Acetic acid (1R,2S,3S,4S,5R,6R)-2,3,4-triacetoxy-6-(7-methoxy-benzo[1,3]dioxol-5-yl)-5-methoxycarbonylamino-cyclohexyl ester (208193-12-8)

Guidance literature:

Multi-step reaction with 16 steps

1: H₂ / Pd/C

2: H₃O⁽¹⁺⁾, MeOH

3: lithium (+)-bis(α-methylbenzyl)amide, LiCl / tetrahydrofuran / -78 °C

4: TMSN₃, (PhIO)n / CH₂Cl₂ / -15 °C

5: LiAlH₄ / diethyl ether

6: pyridine

7: imidazole / CH₂Cl₂

8: H₃O⁺

9: t-BuOK / hexamethylphosphoric acid triamide / 90 °C

10: Et₃N

12: H₂O₂, pyridine

13: H₂O₂, NaHCO₃ / methanol; tetrahydrofuran

14: L-selectride / tetrahydrofuran

15: aq. PhCO₂Na

16: pyridine

With pyridine; 1H-imidazole; methanol; sodium benzoate; lithium aluminium tetrahydride; trimethylsilylazide; (+)-bis(α-methylbenzyl)amine lithium salt; (PhIO)n; oxonium; potassium tert-butylate; hydrogen; dihydrogen peroxide; L-Selectride; sodium hydrogencarbonate; triethylamine; lithium chloride; palladium on activated charcoal; In tetrahydrofuran; methanol; N,N,N,N,N,N-hexamethylphosphoric triamide; diethyl ether; dichloromethane;

DOI:10.1021/ja980407s

upstream raw materials:

acetic anhydride

[(1R,2S,3S,4S,5R,6R)-2,3,4,5-Tetrahydroxy-6-(7-methoxy-benzo[1,3]dioxol-5-yl)-cyclohexyl]-carbamic acid methyl ester

[(1S,2R,3R,4S,6S)-4-Hydroxy-2-(7-methoxy-benzo[1,3]dioxol-5-yl)-5-oxo-7-oxa-bicyclo[4.1.0]hept-3-yl]-carbamic acid methyl ester

[(1S,2R,3R,4S,5S,6R)-4,5-Dihydroxy-2-(7-methoxy-benzo[1,3]dioxol-5-yl)-7-oxa-bicyclo[4.1.0]hept-3-yl]-carbamic acid methyl ester

Downstream raw materials:

pancratistatin

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