Acetic acid (R)-(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

Base Information

Chemical Name:Acetic acid (R)-(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
CAS No.:393803-77-5
Molecular Formula:C₄₀H₄₈O₈
Molecular Weight:656.816
Hs Code.:

Acetic acid (R)-(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

Synonyms:Acetic acid (R)-(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

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Chemical Property of Acetic acid (R)-(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

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Technology Process of Acetic acid (R)-(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

There total 12 articles about Acetic acid (R)-(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 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: 87.0%

: 393803-76-4
Acetic acid (R)-(6-acetoxy-3,4-bis-benzyloxy-2-methyl-phenyl)-[(1aR,3aS,5S,7aS,7bR)-5-(tert-butyl-dimethyl-silanyloxy)-1a,4,4,7a-tetramethyl-octahydro-1-oxa-cyclopropa[a]naphthalen-7b-yl]-methyl ester

: 393803-77-5
Acetic acid (R)-(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

Guidance literature:: With hydrogen fluoride; In acetonitrile; at 0 ℃;
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

: 393803-77-5
Acetic acid (R)-(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

Guidance literature:: Multi-step reaction with 6 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

With pyridine; dmap; hydrogen fluoride; tert.-butyl lithium; sodium methylate; diisobutylaluminium hydride; In methanol; 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

: 393803-77-5
Acetic acid (R)-(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

Guidance literature:: Multi-step reaction with 5 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

With pyridine; dmap; hydrogen fluoride; tert.-butyl lithium; diisobutylaluminium hydride; In diethyl ether; toluene; acetonitrile; pentane;
DOI:10.1021/ol016960n