3-Methyl-but-2-enoic acid (1aR,3aS,5S,7aS,7bR)-7b-[(S)-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

Base Information

Chemical Name:3-Methyl-but-2-enoic acid (1aR,3aS,5S,7aS,7bR)-7b-[(S)-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
CAS No.:393803-70-8
Molecular Formula:C₄₅H₅₄O₉
Molecular Weight:738.918
Hs Code.:

3-Methyl-but-2-enoic acid (1aR,3aS,5S,7aS,7bR)-7b-[(S)-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

Synonyms:3-Methyl-but-2-enoic acid (1aR,3aS,5S,7aS,7bR)-7b-[(S)-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

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Chemical Property of 3-Methyl-but-2-enoic acid (1aR,3aS,5S,7aS,7bR)-7b-[(S)-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

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Technology Process of 3-Methyl-but-2-enoic acid (1aR,3aS,5S,7aS,7bR)-7b-[(S)-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

There total 13 articles about 3-Methyl-but-2-enoic acid (1aR,3aS,5S,7aS,7bR)-7b-[(S)-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 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: 89.0%

: 3350-78-5
3,3-Dimethylacryloyl chloride

: 393803-65-1
Acetic acid (S)-(6-acetoxy-3,4-bis-benzyloxy-2-methyl-phenyl)-((1aR,3aS,5S,7aS,7bR)-5-hydroxy-1a,4,4,7a-tetramethyl-octahydro-1-oxa-cyclopropa[a]naphthalen-7b-yl)-methyl ester

: 393803-70-8
3-Methyl-but-2-enoic acid (1aR,3aS,5S,7aS,7bR)-7b-[(S)-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

Guidance literature:: With N-benzyl-N,N,N-triethylammonium chloride; sodium carbonate; In tetrachloromethane; for 11h; Heating;
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

: 393803-70-8
3-Methyl-but-2-enoic acid (1aR,3aS,5S,7aS,7bR)-7b-[(S)-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

Guidance literature:: Multi-step reaction with 7 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: 48 percent / diethyl ether; pentane / 0.5 h / -78 °C

5.1: 95 percent / DMAP; pyridine / 3 h / 20 °C

6.1: 84 percent / aq. HF / acetonitrile / 23 h / 0 °C

7.1: 89 percent / Na₂CO₃; triethylbenzylammonium chloride / CCl₄ / 11 h / Heating

With pyridine; dmap; hydrogen fluoride; N-benzyl-N,N,N-triethylammonium chloride; tert.-butyl lithium; sodium methylate; diisobutylaluminium hydride; sodium carbonate; In methanol; tetrachloromethane; diethyl ether; 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

: 393803-70-8
3-Methyl-but-2-enoic acid (1aR,3aS,5S,7aS,7bR)-7b-[(S)-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

Guidance literature:: Multi-step reaction with 6 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: 48 percent / diethyl ether; pentane / 0.5 h / -78 °C

4.1: 95 percent / DMAP; pyridine / 3 h / 20 °C

5.1: 84 percent / aq. HF / acetonitrile / 23 h / 0 °C

6.1: 89 percent / Na₂CO₃; triethylbenzylammonium chloride / CCl₄ / 11 h / Heating

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