methyl 1α-(benzyloxy)-6β-(3'-hydroxyprop-2'-en-1'-yl)-5α-methyl-1,2,3,4,4aβ,5,6,8aα-octahydronaphthalene-5β-carboxylate

Base Information

Chemical Name:methyl 1α-(benzyloxy)-6β-(3'-hydroxyprop-2'-en-1'-yl)-5α-methyl-1,2,3,4,4aβ,5,6,8aα-octahydronaphthalene-5β-carboxylate
CAS No.:100818-84-6
Molecular Formula:C₂₃H₃₀O₄
Molecular Weight:370.489
Hs Code.:

Synonyms:methyl 1α-(benzyloxy)-6β-(3'-hydroxyprop-2'-en-1'-yl)-5α-methyl-1,2,3,4,4aβ,5,6,8aα-octahydronaphthalene-5β-carboxylate

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Chemical Property of methyl 1α-(benzyloxy)-6β-(3'-hydroxyprop-2'-en-1'-yl)-5α-methyl-1,2,3,4,4aβ,5,6,8aα-octahydronaphthalene-5β-carboxylate

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Technology Process of methyl 1α-(benzyloxy)-6β-(3'-hydroxyprop-2'-en-1'-yl)-5α-methyl-1,2,3,4,4aβ,5,6,8aα-octahydronaphthalene-5β-carboxylate

There total 15 articles about methyl 1α-(benzyloxy)-6β-(3'-hydroxyprop-2'-en-1'-yl)-5α-methyl-1,2,3,4,4aβ,5,6,8aα-octahydronaphthalene-5β-carboxylate 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: 86.0%

: 100818-82-4
methyl 1α-(benzyloxy)-8-bromo-6β-(3'-hydroxyprop-2'-en-1'-yl)-5α-methyl-1,2,3,4aβ,5,6,8aα-octahydronaphthalene-5β-carboxylate

: 100818-84-6
methyl 1α-(benzyloxy)-6β-(3'-hydroxyprop-2'-en-1'-yl)-5α-methyl-1,2,3,4,4aβ,5,6,8aα-octahydronaphthalene-5β-carboxylate

Guidance literature:: With sodium amalgam; In methanol; at 23 ℃; for 24h;
DOI:10.1021/jo00003a049

Reference yield:

: 100818-74-4
2,3-dideoxy-5,6-O-(1-methylethylidene)-4-O-bnezyl-D-erythro-hexitol

: 100818-84-6
methyl 1α-(benzyloxy)-6β-(3'-hydroxyprop-2'-en-1'-yl)-5α-methyl-1,2,3,4,4aβ,5,6,8aα-octahydronaphthalene-5β-carboxylate

Guidance literature:: Multi-step reaction with 7 steps

1: 1.) MsCl, Et₃N / 2.) Bu₄NI / 1.) 0 deg C, 2.) DMF, 80 deg C

2: 1.) CH₃COOH, CH₃OH, 2.) NaIO₄ / 1.) reflux 2.) THF, H₂O

4: 67 percent / LDA / tetrahydrofuran / -78 - 23 °C

5: 1.) DIBAL-H / 1.) toluene, -78 deg C, 2.) CH₂Cl₂, RT

7: 86 percent / 5percent Na/Hg / methanol / 24 h / 23 °C

With methanol; sodium periodate; sodium amalgam; diisobutylaluminium hydride; acetic acid; methanesulfonyl chloride; triethylamine; lithium diisopropyl amide; tetra-(n-butyl)ammonium iodide; In tetrahydrofuran; methanol;
DOI:10.1016/S0040-4039(00)98725-2

Reference yield:

: 87604-53-3
(R)-4-((S)-1-(benzyloxy)but-3-ene-1-yl)-2,2-dimethyl-1,3-dioxypentane

: 100818-84-6
methyl 1α-(benzyloxy)-6β-(3'-hydroxyprop-2'-en-1'-yl)-5α-methyl-1,2,3,4,4aβ,5,6,8aα-octahydronaphthalene-5β-carboxylate

Guidance literature:: Multi-step reaction with 8 steps

1: 1.) BH₃ 2.) 3M NaOH, 30 percent H₂O₂ / 1.) THF, 0 deg C

2: 1.) MsCl, Et₃N / 2.) Bu₄NI / 1.) 0 deg C, 2.) DMF, 80 deg C

3: 1.) CH₃COOH, CH₃OH, 2.) NaIO₄ / 1.) reflux 2.) THF, H₂O

5: 67 percent / LDA / tetrahydrofuran / -78 - 23 °C

6: 1.) DIBAL-H / 1.) toluene, -78 deg C, 2.) CH₂Cl₂, RT

8: 86 percent / 5percent Na/Hg / methanol / 24 h / 23 °C

With methanol; sodium hydroxide; sodium periodate; sodium amalgam; borane; dihydrogen peroxide; diisobutylaluminium hydride; acetic acid; methanesulfonyl chloride; triethylamine; lithium diisopropyl amide; tetra-(n-butyl)ammonium iodide; In tetrahydrofuran; methanol;
DOI:10.1016/S0040-4039(00)98725-2