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

Base Information

Chemical Name:(1R,2S,3R,4R,5S)-5-(tert-Butyl-dimethyl-silanyloxy)-5-hydroxymethyl-cyclohexane-1,2,3,4-tetraol
CAS No.:504397-88-0
Molecular Formula:C₁₃H₂₈O₆Si
Molecular Weight:308.447
Hs Code.:

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

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

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

There total 5 articles about (1R,2S,3R,4R,5S)-5-(tert-Butyl-dimethyl-silanyloxy)-5-hydroxymethyl-cyclohexane-1,2,3,4-tetraol 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: 55.0%

: 356760-84-4
(1R,2R,3R,4S,5R)-1-(tert-butyldimethylsilyloxy)-2,4,5-trihydroxycyclohexane-1,3-carbolactone

: 504397-88-0
(1R,2S,3R,4R,5S)-5-(tert-Butyl-dimethyl-silanyloxy)-5-hydroxymethyl-cyclohexane-1,2,3,4-tetraol

: 504397-89-1
(1S,2R,3R,4S,5R)-1-(tert-Butyl-dimethyl-silanyloxymethyl)-cyclohexane-1,2,3,4,5-pentaol

Guidance literature:: With lithium borohydride; In tetrahydrofuran; methanol; for 7h; Heating;
DOI:10.1021/jo026692m

Reference yield:

: 105539-79-5
1(R)-4-exo-(benzoyloxy)-1-<<(1,1-dimethylethyl)dimethylsilyl>oxy>-6-oxabicyclo<3.2.1>oct-2-en-7-one

: 504397-88-0
(1R,2S,3R,4R,5S)-5-(tert-Butyl-dimethyl-silanyloxy)-5-hydroxymethyl-cyclohexane-1,2,3,4-tetraol

Guidance literature:: Multi-step reaction with 3 steps

1: 8 percent / potassium cyanide / 1 h / 20 °C

2: 45 percent / sodium periodate / osmium tetraoxide / dioxane; H₂O / 6 h / 20 °C

3: 55 percent / lithium borohydride / tetrahydrofuran; methanol / 7 h / Heating

With potassium cyanide; sodium periodate; lithium borohydride; osmium(VIII) oxide; In tetrahydrofuran; 1,4-dioxane; methanol; water;
DOI:10.1021/jo026692m

Reference yield:

: 356760-73-1
methyl (1R,3R,4R)-1-(tert-butyldimethylsilyloxy)-3,4-dihydroxycyclohex-5-ene-1-carboxylate

: 504397-88-0
(1R,2S,3R,4R,5S)-5-(tert-Butyl-dimethyl-silanyloxy)-5-hydroxymethyl-cyclohexane-1,2,3,4-tetraol

Guidance literature:: Multi-step reaction with 3 steps

1: 83 percent / sodium hydride / tetrahydrofuran / 0.25 h / 0 °C

2: 45 percent / sodium periodate / osmium tetraoxide / dioxane; H₂O / 6 h / 20 °C

3: 55 percent / lithium borohydride / tetrahydrofuran; methanol / 7 h / Heating

With sodium periodate; lithium borohydride; sodium hydride; osmium(VIII) oxide; In tetrahydrofuran; 1,4-dioxane; methanol; water;
DOI:10.1021/jo026692m