(1S,2S,4R,7S,9R,10S)-12,12-dimethyl-4-phenyl-9-tosyloxy-3,5,11,13-tetra-oxatricyclo[8.3.0.0^2,7]tridecan-7-ol

Base Information

• Chemical Name: (1S,2S,4R,7S,9R,10S)-12,12-dimethyl-4-phenyl-9-tosyloxy-3,5,11,13-tetra-oxatricyclo[8.3.0.0^2,7]tridecan-7-ol
• CAS No.: 693245-43-1
• Molecular Formula: C₂₄H₂₈O₈S
• Molecular Weight: 476.548

Synonyms:(1S,2S,4R,7S,9R,10S)-12,12-dimethyl-4-phenyl-9-tosyloxy-3,5,11,13-tetra-oxatricyclo[8.3.0.0^2,7]tridecan-7-ol

Chemical Property of (1S,2S,4R,7S,9R,10S)-12,12-dimethyl-4-phenyl-9-tosyloxy-3,5,11,13-tetra-oxatricyclo[8.3.0.0^2,7]tridecan-7-ol

Chemical Property:

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Technology Process of (1S,2S,4R,7S,9R,10S)-12,12-dimethyl-4-phenyl-9-tosyloxy-3,5,11,13-tetra-oxatricyclo[8.3.0.0^2,7]tridecan-7-ol

There total 3 articles about (1S,2S,4R,7S,9R,10S)-12,12-dimethyl-4-phenyl-9-tosyloxy-3,5,11,13-tetra-oxatricyclo[8.3.0.0^2,7]tridecan-7-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: 100.0%

p-toluenesulfonyl chloride (98-59-9) + (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) → (1S,2S,4R,7S,9R,10S)-12,12-dimethyl-4-phenyl-9-tosyloxy-3,5,11,13-tetra-oxatricyclo[8.3.0.02,7]tridecan-7-ol (693245-43-1)

Guidance literature:

With pyridine; dmap; at 20 ℃; for 16h;

DOI:10.1039/b314795a

Reference yield:

(1S,3R,6S,8R,9S,10R)-3-phenyl-2,4-dioxabicyclo[4.4.0]decane-6,8,9,10-tetrol (693245-37-3) → (1S,2S,4R,7S,9R,10S)-12,12-dimethyl-4-phenyl-9-tosyloxy-3,5,11,13-tetra-oxatricyclo[8.3.0.02,7]tridecan-7-ol (693245-43-1)

Guidance literature:

Multi-step reaction with 2 steps

1: 41 percent / TsOH*H₂O / dimethylformamide / 4 h / 20 °C

2: 100 percent / pyridine; DMAP / 16 h / 20 °C

With pyridine; dmap; toluene-4-sulfonic acid; In N,N-dimethyl-formamide;

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) → (1S,2S,4R,7S,9R,10S)-12,12-dimethyl-4-phenyl-9-tosyloxy-3,5,11,13-tetra-oxatricyclo[8.3.0.02,7]tridecan-7-ol (693245-43-1)

Guidance literature:

Multi-step reaction with 3 steps

1.1: NaOMe / methanol / 1 h / 20 °C

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

2.1: 41 percent / TsOH*H₂O / dimethylformamide / 4 h / 20 °C

3.1: 100 percent / pyridine; DMAP / 16 h / 20 °C

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

DOI:10.1039/b314795a

upstream raw materials:

p-toluenesulfonyl chloride

(1S,2S,4R,7S,9R,10S)-12,12-dimethyl-4-phenyl-3,5,11,13-tetra-oxatricyclo[8.3.0.0^2,7]tridecane-7,9-diol

(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

Downstream raw materials:

(1S,2S,3R,4S,5S)-1-amino-5-hydroxymethyl-2,3,4,5-tetrahydroxycyclohexane

(1S)-(1(OH),2,4/1,3,5)-5-Amino-1-C-(hydroxymethyl)-1,2,3,4-cyclohexanetetrol

1L-(1,2,4/3,5)-5-acetamido-1-C-(acetoxymethyl)-2,3,4-tri-O-acetyl-1,2,3,4-cyclohexanetetraol

(1S,2S,4R,7S,9S,10S)-9-acetamido-12,12-dimethyl-4-phenyl-3,5,11,13-tetra-oxatricyclo[8.3.0.0^2,7]tridecane-7-ol

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