methyl (1R,3R,4R)-1-(tert-butyldimethylsilyloxy)-3,4-dihydroxycyclohex-5-ene-1-carboxylate

Base Information

• Chemical Name: methyl (1R,3R,4R)-1-(tert-butyldimethylsilyloxy)-3,4-dihydroxycyclohex-5-ene-1-carboxylate
• CAS No.: 356760-73-1
• Molecular Formula: C₁₄H₂₆O₅Si
• Molecular Weight: 302.443

Synonyms:methyl (1R,3R,4R)-1-(tert-butyldimethylsilyloxy)-3,4-dihydroxycyclohex-5-ene-1-carboxylate

Chemical Property of methyl (1R,3R,4R)-1-(tert-butyldimethylsilyloxy)-3,4-dihydroxycyclohex-5-ene-1-carboxylate

Chemical Property:

Purity/Quality:

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Technology Process of methyl (1R,3R,4R)-1-(tert-butyldimethylsilyloxy)-3,4-dihydroxycyclohex-5-ene-1-carboxylate

There total 2 articles about methyl (1R,3R,4R)-1-(tert-butyldimethylsilyloxy)-3,4-dihydroxycyclohex-5-ene-1-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: 94.0%

1(R)-4-exo-(benzoyloxy)-1-<<(1,1-dimethylethyl)dimethylsilyl>oxy>-6-oxabicyclo<3.2.1>oct-2-en-7-one (105539-79-5) → (1R,3R,4R)-1-(tert-butyldimethylsilyloxy)-4-hydroxycyclohex-5-ene-1,3-carbolactone (356760-74-2) + methyl (1R,3R,4R)-1-(tert-butyldimethylsilyloxy)-3,4-dihydroxycyclohex-5-ene-1-carboxylate (356760-73-1)

Guidance literature:

With potassium carbonate; In methanol; at 20 ℃;

DOI:10.1016/S0040-4039(01)00601-3

Reference yield: 89.0%

methanol (67-56-1) + 1(R)-4-exo-(benzoyloxy)-1-<<(1,1-dimethylethyl)dimethylsilyl>oxy>-6-oxabicyclo<3.2.1>oct-2-en-7-one (105539-79-5) → (1R,3R,4R)-1-(tert-butyldimethylsilyloxy)-4-hydroxycyclohex-5-ene-1,3-carbolactone (356760-74-2) + methyl (1R,3R,4R)-1-(tert-butyldimethylsilyloxy)-3,4-dihydroxycyclohex-5-ene-1-carboxylate (356760-73-1)

Guidance literature:

With potassium cyanide; at 20 ℃; for 1h;

DOI:10.1021/jo026692m

Reference yield: 89.0%

methyl (1R,3R,4R)-1-(tert-butyldimethylsilyloxy)-3,4-dihydroxycyclohex-5-ene-1-carboxylate (356760-73-1) → methyl (1R,2R,3R,4S,5R)-1-(tert-butyldimethylsilyloxy)-2,3,4,5-tetrahydroxycyclohexane-1-carboxylate

Guidance literature:

With osmium(VIII) oxide; trimethylamine-N-oxide;

DOI:10.1016/S0040-4039(01)00601-3

upstream raw materials:

1(R)-4-exo-(benzoyloxy)-1-<<(1,1-dimethylethyl)dimethylsilyl>oxy>-6-oxabicyclo<3.2.1>oct-2-en-7-one

methanol

Downstream raw materials:

(1R,2S,3S,4S,5R)-1,2,3,4,5-pentahydroxycyclohexane-1-carboxylic acid

(1R,2S,3R,4R,5S)-5-(tert-Butyl-dimethyl-silanyloxy)-5-hydroxymethyl-cyclohexane-1,2,3,4-tetraol

(1R,2S,3S,4S,5S)-5-(tert-Butyl-dimethyl-silanyloxy)-5-hydroxymethyl-cyclohexane-1,2,3,4-tetraol

(1S,2R,3R,4S,5R)-1-(tert-Butyl-dimethyl-silanyloxymethyl)-cyclohexane-1,2,3,4,5-pentaol

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