(1R,2S,3S,5R,8S,10R)-12,12-dimethyl-5-phenyl-4,6,11,13-tetra-oxatricyclo[8.3.0.0^3,8]tridecane-2,8-diol

Base Information

• Chemical Name: (1R,2S,3S,5R,8S,10R)-12,12-dimethyl-5-phenyl-4,6,11,13-tetra-oxatricyclo[8.3.0.0^3,8]tridecane-2,8-diol
• CAS No.: 693245-44-2
• Molecular Formula: C₁₇H₂₂O₆
• Molecular Weight: 322.358

Synonyms:(1R,2S,3S,5R,8S,10R)-12,12-dimethyl-5-phenyl-4,6,11,13-tetra-oxatricyclo[8.3.0.0^3,8]tridecane-2,8-diol

Chemical Property of (1R,2S,3S,5R,8S,10R)-12,12-dimethyl-5-phenyl-4,6,11,13-tetra-oxatricyclo[8.3.0.0^3,8]tridecane-2,8-diol

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Technology Process of (1R,2S,3S,5R,8S,10R)-12,12-dimethyl-5-phenyl-4,6,11,13-tetra-oxatricyclo[8.3.0.0^3,8]tridecane-2,8-diol

There total 2 articles about (1R,2S,3S,5R,8S,10R)-12,12-dimethyl-5-phenyl-4,6,11,13-tetra-oxatricyclo[8.3.0.0^3,8]tridecane-2,8-diol 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: 41.0%

2-Methoxypropene (116-11-0) + (1S,3R,6S,8R,9S,10R)-3-phenyl-2,4-dioxabicyclo[4.4.0]decane-6,8,9,10-tetrol (693245-37-3) → (1R,2S,3S,5R,8S,10R)-12,12-dimethyl-5-phenyl-4,6,11,13-tetra-oxatricyclo[8.3.0.03,8]tridecane-2,8-diol (693245-44-2) + (1S,2S,4R,7S,9R,10S)-12,12-dimethyl-4-phenyl-3,5,11,13-tetra-oxatricyclo[8.3.0.02,7]tridecane-7,9-diol (693245-41-9)

Guidance literature:

With toluene-4-sulfonic acid; In N,N-dimethyl-formamide; at 20 ℃; for 4h;

DOI:10.1039/b314795a

Reference yield:

1L-(1,2,4/3,5)-1-C-(acetoxymethyl)-2,3,4,5-tetra-O-acetyl-1,2,3,4,5-cyclohexanepentol (694527-29-2) → (1R,2S,3S,5R,8S,10R)-12,12-dimethyl-5-phenyl-4,6,11,13-tetra-oxatricyclo[8.3.0.03,8]tridecane-2,8-diol (693245-44-2)

Guidance literature:

Multi-step reaction with 2 steps

1.1: NaOMe / methanol / 1 h / 20 °C

1.2: 59 percent / p-TsOH*H₂O / dimethylformamide / 3 h / 50 °C

2.1: 36 percent / TsOH*H₂O / dimethylformamide / 4 h / 20 °C

With sodium methylate; toluene-4-sulfonic acid; In methanol; N,N-dimethyl-formamide;

DOI:10.1039/b314795a

Reference yield:

acetic anhydride (108-24-7) + (1R,2S,3S,5R,8S,10R)-12,12-dimethyl-5-phenyl-4,6,11,13-tetra-oxatricyclo[8.3.0.03,8]tridecane-2,8-diol (693245-44-2) → (1R,2S,3S,5R,8S,10R)-2-acetoxy-12,12-dimethyl-5-phenyl-4,6,11,13-tetra-oxatricyclo[8.3.0.03,8]tridecan-8-ol

Guidance literature:

With pyridine; at 20 ℃;

DOI:10.1039/b314795a

upstream raw materials:

2-Methoxypropene

(1S,3R,6S,8R,9S,10R)-3-phenyl-2,4-dioxabicyclo[4.4.0]decane-6,8,9,10-tetrol

1L-(1,2,4/3,5)-1-C-(acetoxymethyl)-2,3,4,5-tetra-O-acetyl-1,2,3,4,5-cyclohexanepentol

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