(3R,5R)-5-[(tert-butyldimethylsilyl)oxy]-1,3-dihydroxy-4-methylene-cyclohexanecarboxylic acid methyl ester

Base Information

Chemical Name:(3R,5R)-5-[(tert-butyldimethylsilyl)oxy]-1,3-dihydroxy-4-methylene-cyclohexanecarboxylic acid methyl ester
CAS No.:852380-64-4
Molecular Formula:C₁₅H₂₈O₅Si
Molecular Weight:316.47
Hs Code.:

Synonyms:(3R,5R)-5-[(tert-butyldimethylsilyl)oxy]-1,3-dihydroxy-4-methylene-cyclohexanecarboxylic acid methyl ester

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Chemical Property of (3R,5R)-5-[(tert-butyldimethylsilyl)oxy]-1,3-dihydroxy-4-methylene-cyclohexanecarboxylic acid methyl ester

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Technology Process of (3R,5R)-5-[(tert-butyldimethylsilyl)oxy]-1,3-dihydroxy-4-methylene-cyclohexanecarboxylic acid methyl ester

There total 6 articles about (3R,5R)-5-[(tert-butyldimethylsilyl)oxy]-1,3-dihydroxy-4-methylene-cyclohexanecarboxylic acid methyl ester 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: 79.0%

: (1R,3R,5R)-1-acetoxy-3-[(tert-butyldimethylsilyl)oxy]-4-methylene-6-oxabicyclo[3.2.1]octan-7-one

: 852380-64-4
(3R,5R)-5-[(tert-butyldimethylsilyl)oxy]-1,3-dihydroxy-4-methylene-cyclohexanecarboxylic acid methyl ester

Guidance literature:: With sodium methylate; In methanol; at 20 ℃; for 17h; Inert atmosphere;

Reference yield: 79.0%

: (1R,3R,5R)-1-acetoxy-3-[(tert-butyldimethylsilyl)oxy]-4-methylene-6-oxabicyclo[3.2.1]octan-7-one

: 124-41-4
sodium methylate

: 852380-64-4
(3R,5R)-5-[(tert-butyldimethylsilyl)oxy]-1,3-dihydroxy-4-methylene-cyclohexanecarboxylic acid methyl ester

Guidance literature:: With methanol; at 20 ℃; for 17h; Inert atmosphere;

Reference yield:

: 77-95-2
D-(-)-quinic acid

: 852380-64-4
(3R,5R)-5-[(tert-butyldimethylsilyl)oxy]-1,3-dihydroxy-4-methylene-cyclohexanecarboxylic acid methyl ester

Guidance literature:: Multi-step reaction with 5 steps

1: Amberlyst H⁺ resin; benzene / dimethylformamide / Heating

2: triethylamine; DMAP / dimethylformamide / 23 °C

3: pyridinium dichromate; Celite; molecular sieves 4 Angstroem / acetonitrile / 45 °C

4: t-BuOK / tetrahydrofuran / 65 °C

5: 74 percent / molecular sieves 4 Angstroem / 5.5 h / 23 °C

With dmap; dipyridinium dichromate; 4 A molecular sieve; Amberlyst H⁺ resin; Celite; potassium tert-butylate; triethylamine; benzene; In tetrahydrofuran; N,N-dimethyl-formamide; acetonitrile; 4: Wittig olefination;
DOI:10.1021/ja050586v