(3S,4R,5S,8S)-8-(3-Benzyloxy-phenyl)-8-methoxy-3,5-dimethyl-oct-1-yn-4-ol

Base Information

• Chemical Name: (3S,4R,5S,8S)-8-(3-Benzyloxy-phenyl)-8-methoxy-3,5-dimethyl-oct-1-yn-4-ol
• CAS No.: 159751-72-1
• Molecular Formula: C₂₄H₃₀O₃
• Molecular Weight: 366.5

Synonyms:(3S,4R,5S,8S)-8-(3-Benzyloxy-phenyl)-8-methoxy-3,5-dimethyl-oct-1-yn-4-ol

Chemical Property of (3S,4R,5S,8S)-8-(3-Benzyloxy-phenyl)-8-methoxy-3,5-dimethyl-oct-1-yn-4-ol

Chemical Property:

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Technology Process of (3S,4R,5S,8S)-8-(3-Benzyloxy-phenyl)-8-methoxy-3,5-dimethyl-oct-1-yn-4-ol

There total 2 articles about (3S,4R,5S,8S)-8-(3-Benzyloxy-phenyl)-8-methoxy-3,5-dimethyl-oct-1-yn-4-ol 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: 72.0%

(4R,5R,6R)-4-[(1S,4S)-4-(3-Benzyloxy-phenyl)-4-methoxy-1-methyl-butyl]-6-chloromethyl-2,2,5-trimethyl-[1,3]dioxane (159751-71-0) → (3S,4R,5S,8S)-8-(3-Benzyloxy-phenyl)-8-methoxy-3,5-dimethyl-oct-1-yn-4-ol (159751-72-1)

Guidance literature:

With lithium diisopropyl amide; In tetrahydrofuran;

DOI:10.1016/S0040-4039(00)73355-7

Reference yield:

{(4R,5R,6R)-6-[(1S,4S)-4-(3-Benzyloxy-phenyl)-4-methoxy-1-methyl-butyl]-2,2,5-trimethyl-[1,3]dioxan-4-yl}-methanol → (3S,4R,5S,8S)-8-(3-Benzyloxy-phenyl)-8-methoxy-3,5-dimethyl-oct-1-yn-4-ol (159751-72-1)

Guidance literature:

Multi-step reaction with 2 steps

1: 99 percent / Ph₃P, CCl₄ / Heating

2: 72 percent / LDA / tetrahydrofuran

With tetrachloromethane; triphenylphosphine; lithium diisopropyl amide; In tetrahydrofuran;

DOI:10.1016/S0040-4039(00)73355-7

Reference yield: 87.0%

chloromethyl methyl ether (107-30-2) + (3S,4R,5S,8S)-8-(3-Benzyloxy-phenyl)-8-methoxy-3,5-dimethyl-oct-1-yn-4-ol (159751-72-1) → 1-Benzyloxy-3-((1S,4S,5R,6S)-1-methoxy-5-methoxymethoxy-4,6-dimethyl-oct-7-ynyl)-benzene (159751-73-2)

Guidance literature:

With N-ethyl-N,N-diisopropylamine; In dichloromethane;

DOI:10.1016/S0040-4039(00)73355-7

upstream raw materials:

(4R,5R,6R)-4-[(1S,4S)-4-(3-Benzyloxy-phenyl)-4-methoxy-1-methyl-butyl]-6-chloromethyl-2,2,5-trimethyl-[1,3]dioxane

Downstream raw materials:

1-Benzyloxy-3-((1S,4S,5R,6S)-1-methoxy-5-methoxymethoxy-4,6-dimethyl-oct-7-ynyl)-benzene

(R)-2-[(3S,4R,5S,8S)-8-(3-Benzyloxy-phenyl)-4-hydroxy-8-methoxy-3,5-dimethyl-oct-1-ynyl]-3,3,5-trimethyl-6-oxo-cyclohex-1-enecarbaldehyde

(R)-2-[(3S,4R,5S,8S)-8-(3-Benzyloxy-phenyl)-4-hydroxy-8-methoxy-3,5-dimethyl-oct-1-ynyl]-3,3,5-trimethyl-6-oxo-cyclohex-1-enecarboxylic acid

(R)-2-[(3S,4R,5S,8S)-8-(3-Benzyloxy-phenyl)-8-methoxy-4-methoxymethoxy-3,5-dimethyl-oct-1-ynyl]-3,3,5-trimethyl-6-oxo-cyclohex-1-enecarbaldehyde

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