3-Methyl-but-2-enoic acid (1aR,3aS,5S,7aS,7bR)-7b-[(R)-acetoxy-(6-acetoxy-3,4-dihydroxy-2-methyl-phenyl)-methyl]-1a,4,4,7a-tetramethyl-decahydro-1-oxa-cyclopropa[a]naphthalen-5-yl ester

Base Information

Chemical Name:3-Methyl-but-2-enoic acid (1aR,3aS,5S,7aS,7bR)-7b-[(R)-acetoxy-(6-acetoxy-3,4-dihydroxy-2-methyl-phenyl)-methyl]-1a,4,4,7a-tetramethyl-decahydro-1-oxa-cyclopropa[a]naphthalen-5-yl ester
CAS No.:393803-81-1
Molecular Formula:C₃₁H₄₂O₉
Molecular Weight:558.669
Hs Code.:

3-Methyl-but-2-enoic acid (1aR,3aS,5S,7aS,7bR)-7b-[(R)-acetoxy-(6-acetoxy-3,4-dihydroxy-2-methyl-phenyl)-methyl]-1a,4,4,7a-tetramethyl-decahydro-1-oxa-cyclopropa[a]naphthalen-5-yl ester

Synonyms:3-Methyl-but-2-enoic acid (1aR,3aS,5S,7aS,7bR)-7b-[(R)-acetoxy-(6-acetoxy-3,4-dihydroxy-2-methyl-phenyl)-methyl]-1a,4,4,7a-tetramethyl-decahydro-1-oxa-cyclopropa[a]naphthalen-5-yl ester

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Chemical Property of 3-Methyl-but-2-enoic acid (1aR,3aS,5S,7aS,7bR)-7b-[(R)-acetoxy-(6-acetoxy-3,4-dihydroxy-2-methyl-phenyl)-methyl]-1a,4,4,7a-tetramethyl-decahydro-1-oxa-cyclopropa[a]naphthalen-5-yl ester

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Technology Process of 3-Methyl-but-2-enoic acid (1aR,3aS,5S,7aS,7bR)-7b-[(R)-acetoxy-(6-acetoxy-3,4-dihydroxy-2-methyl-phenyl)-methyl]-1a,4,4,7a-tetramethyl-decahydro-1-oxa-cyclopropa[a]naphthalen-5-yl ester

There total 15 articles about 3-Methyl-but-2-enoic acid (1aR,3aS,5S,7aS,7bR)-7b-[(R)-acetoxy-(6-acetoxy-3,4-dihydroxy-2-methyl-phenyl)-methyl]-1a,4,4,7a-tetramethyl-decahydro-1-oxa-cyclopropa[a]naphthalen-5-yl 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: 35.0%

: 393803-80-0
3-Methyl-but-2-enoic acid (1aR,3aS,5S,7aS,7bR)-7b-[(R)-acetoxy-(6-acetoxy-3,4-bis-benzyloxy-2-methyl-phenyl)-methyl]-1a,4,4,7a-tetramethyl-decahydro-1-oxa-cyclopropa[a]naphthalen-5-yl ester

: 393803-81-1
3-Methyl-but-2-enoic acid (1aR,3aS,5S,7aS,7bR)-7b-[(R)-acetoxy-(6-acetoxy-3,4-dihydroxy-2-methyl-phenyl)-methyl]-1a,4,4,7a-tetramethyl-decahydro-1-oxa-cyclopropa[a]naphthalen-5-yl ester

Guidance literature:: With cyclohexene; palladium on activated charcoal; In ethanol; at 80 ℃;
DOI:10.1021/ol016960n

Reference yield:

: 114626-74-3
(1aR,3aS,5S,7aS,7bS)-5-Acetoxy-1a,4,4,7a-tetramethyl-octahydro-1-oxa-cyclopropa[a]naphthalene-7b-carboxylic acid methyl ester

: 393803-81-1
3-Methyl-but-2-enoic acid (1aR,3aS,5S,7aS,7bR)-7b-[(R)-acetoxy-(6-acetoxy-3,4-dihydroxy-2-methyl-phenyl)-methyl]-1a,4,4,7a-tetramethyl-decahydro-1-oxa-cyclopropa[a]naphthalen-5-yl ester

Guidance literature:: Multi-step reaction with 8 steps

1.1: 286 mg / NaOMe / methanol / 22 h / 20 °C

2.1: 86 percent / pyridine / 1 h / 0 °C

3.1: 70 percent / Dibal-H / toluene / 0.5 h / -78 °C

4.1: t-BuLi / diethyl ether; pentane / 1 h / -78 °C

4.2: 15 percent / diethyl ether; pentane / 0.5 h / -78 °C

5.1: 90 percent / DMAP; pyridine / 20 °C

6.1: 87 percent / aq. HF / acetonitrile / 0 °C

7.1: 86 percent / Na₂CO₃; triethylbenzylammonium chloride / CCl₄ / Heating

8.1: 35 percent / cyclohexene / Pd/C / ethanol / 80 °C

With pyridine; dmap; hydrogen fluoride; N-benzyl-N,N,N-triethylammonium chloride; tert.-butyl lithium; sodium methylate; diisobutylaluminium hydride; sodium carbonate; cyclohexene; palladium on activated charcoal; In methanol; tetrachloromethane; diethyl ether; ethanol; toluene; acetonitrile; pentane;
DOI:10.1021/ol016960n

Reference yield:

: 393803-33-3
(1aR,3aS,5S,7aS,7bS)-5-Hydroxy-1a,4,4,7a-tetramethyl-octahydro-1-oxa-cyclopropa[a]naphthalene-7b-carboxylic acid methyl ester

: 393803-81-1
3-Methyl-but-2-enoic acid (1aR,3aS,5S,7aS,7bR)-7b-[(R)-acetoxy-(6-acetoxy-3,4-dihydroxy-2-methyl-phenyl)-methyl]-1a,4,4,7a-tetramethyl-decahydro-1-oxa-cyclopropa[a]naphthalen-5-yl ester

Guidance literature:: Multi-step reaction with 7 steps

1.1: 86 percent / pyridine / 1 h / 0 °C

2.1: 70 percent / Dibal-H / toluene / 0.5 h / -78 °C

3.1: t-BuLi / diethyl ether; pentane / 1 h / -78 °C

3.2: 15 percent / diethyl ether; pentane / 0.5 h / -78 °C

4.1: 90 percent / DMAP; pyridine / 20 °C

5.1: 87 percent / aq. HF / acetonitrile / 0 °C

6.1: 86 percent / Na₂CO₃; triethylbenzylammonium chloride / CCl₄ / Heating

7.1: 35 percent / cyclohexene / Pd/C / ethanol / 80 °C

With pyridine; dmap; hydrogen fluoride; N-benzyl-N,N,N-triethylammonium chloride; tert.-butyl lithium; diisobutylaluminium hydride; sodium carbonate; cyclohexene; palladium on activated charcoal; In tetrachloromethane; diethyl ether; ethanol; toluene; acetonitrile; pentane;
DOI:10.1021/ol016960n