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

Base Information

• Chemical Name: (1S,3R,6S,8R,9S,10R)-3-phenyl-2,4-dioxabicyclo[4.4.0]decane-6,8,9,10-tetrol
• CAS No.: 693245-37-3
• Molecular Formula: C₁₄H₁₈O₆
• Molecular Weight: 282.293

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

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

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

There total 1 articles about (1S,3R,6S,8R,9S,10R)-3-phenyl-2,4-dioxabicyclo[4.4.0]decane-6,8,9,10-tetrol 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: 59.0%

benzaldehyde dimethyl acetal (1125-88-8) + 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) → (2R,5S,6S,7R,8S,9R)-2-phenyl-1,3-dioxaspiro-[4.5]decane-6,7,8,9-tetrol + (2S,5S,6S,7R,8S,9R)-2-phenyl-1,3-dioxaspiro-[4.5]decane-6,7,8,9-tetrol + (1S,3R,6S,8R,9S,10R)-3-phenyl-2,4-dioxabicyclo[4.4.0]decane-6,8,9,10-tetrol (693245-37-3)

Guidance literature:

1L-(1,2,4/3,5)-1-C-(acetoxymethyl)-2,3,4,5-tetra-O-acetyl-1,2,3,4,5-cyclohexanepentol; With sodium methylate; In methanol; at 20 ℃; for 1h;

benzaldehyde dimethyl acetal; With toluene-4-sulfonic acid; In N,N-dimethyl-formamide; at 50 ℃; for 3h;

DOI:10.1039/b314795a

Reference yield: 92.0%

acetic anhydride (108-24-7) + (1S,3R,6S,8R,9S,10R)-3-phenyl-2,4-dioxabicyclo[4.4.0]decane-6,8,9,10-tetrol (693245-37-3) → (1S,3R,6S,8R,9S,10R)-8,9,10-triacetoxy-3-phenyl-2,4-dioxabicyclo[4.4.0]decan-6-ol

Guidance literature:

With pyridine; at 20 ℃; for 17h;

DOI:10.1039/b314795a

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

upstream raw materials:

benzaldehyde dimethyl acetal

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:

(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

(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,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

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