(1S,3R,4R,5R)-3-Benzyloxymethoxy-1-(tert-butyl-dimethyl-silanyloxy)-4-hydroxy-5-(2-hydroxy-ethyl)-cyclohexanecarboxylic acid methyl ester

Base Information

Chemical Name:(1S,3R,4R,5R)-3-Benzyloxymethoxy-1-(tert-butyl-dimethyl-silanyloxy)-4-hydroxy-5-(2-hydroxy-ethyl)-cyclohexanecarboxylic acid methyl ester
CAS No.:160912-04-9
Molecular Formula:C₂₄H₄₀O₇Si
Molecular Weight:468.663
Hs Code.:

Synonyms:(1S,3R,4R,5R)-3-Benzyloxymethoxy-1-(tert-butyl-dimethyl-silanyloxy)-4-hydroxy-5-(2-hydroxy-ethyl)-cyclohexanecarboxylic acid methyl ester

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Chemical Property of (1S,3R,4R,5R)-3-Benzyloxymethoxy-1-(tert-butyl-dimethyl-silanyloxy)-4-hydroxy-5-(2-hydroxy-ethyl)-cyclohexanecarboxylic acid methyl ester

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Technology Process of (1S,3R,4R,5R)-3-Benzyloxymethoxy-1-(tert-butyl-dimethyl-silanyloxy)-4-hydroxy-5-(2-hydroxy-ethyl)-cyclohexanecarboxylic acid methyl ester

There total 8 articles about (1S,3R,4R,5R)-3-Benzyloxymethoxy-1-(tert-butyl-dimethyl-silanyloxy)-4-hydroxy-5-(2-hydroxy-ethyl)-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: 100.0%

: (3aS,5S,7R,7aR)-7-Benzyloxymethoxy-5-(tert-butyl-dimethyl-silanyloxy)-2-hydroxy-octahydro-benzofuran-5-carboxylic acid methyl ester

: 160912-04-9
(1S,3R,4R,5R)-3-Benzyloxymethoxy-1-(tert-butyl-dimethyl-silanyloxy)-4-hydroxy-5-(2-hydroxy-ethyl)-cyclohexanecarboxylic acid methyl ester

Guidance literature:: With sodium tetrahydroborate; In methanol; at 0 ℃; for 0.0833333h;
DOI:10.1021/jo00102a025

Reference yield:

: 105539-80-8
methyl<1(R)-(1α,4α,5β)>-4-(benzoyloxy)-1-<<(1,1-dimethylethyl)dimethylsilyl>oxy>-5-hydroxy-2-cyclohexene-1-carboxylate

: 160912-04-9
(1S,3R,4R,5R)-3-Benzyloxymethoxy-1-(tert-butyl-dimethyl-silanyloxy)-4-hydroxy-5-(2-hydroxy-ethyl)-cyclohexanecarboxylic acid methyl ester

Guidance literature:: Multi-step reaction with 6 steps

1: 97 percent / i-Pr₂NEt / CH₂Cl₂ / 15 h / Ambient temperature

2: 72 percent / MeONa / tetrahydrofuran; methanol / 0.25 h / Ambient temperature

3: Et₃N / CH₂Cl₂ / 1.) -78 deg C, 30 min, 2.) r.t., 12 h

4: 78 percent / Bu₃SnH, AIBN / benzene / 18 h / Heating

5: 74 percent / 1.5percent aq. HCl / tetrahydrofuran / 24 h / Ambient temperature

6: 100 percent / NaBH₄ / methanol / 0.08 h / 0 °C

With hydrogenchloride; sodium tetrahydroborate; 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride; sodium methylate; triethylamine; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; methanol; dichloromethane; benzene;
DOI:10.1021/jo00102a025

Reference yield:

: 1054663-14-7
(3aR,5S,7R,7aR)-7-Benzyloxymethoxy-5-(tert-butyl-dimethyl-silanyloxy)-2,2-dimethyl-octahydro-benzo[d][1,2]oxasilole-5-carboxylic acid methyl ester

: 160912-04-9
(1S,3R,4R,5R)-3-Benzyloxymethoxy-1-(tert-butyl-dimethyl-silanyloxy)-4-hydroxy-5-(2-hydroxy-ethyl)-cyclohexanecarboxylic acid methyl ester

Guidance literature:: Multi-step reaction with 5 steps

1: 30percent aq. H₂O₂, NaHCO₃ / methanol; tetrahydrofuran / 5 h / Heating

2: Et₃N / CH₂Cl₂ / 1.) -78 deg C, 30 min, 2.) r.t., 12 h

3: 78 percent / Bu₃SnH, AIBN / benzene / 18 h / Heating

4: 74 percent / 1.5percent aq. HCl / tetrahydrofuran / 24 h / Ambient temperature

5: 100 percent / NaBH₄ / methanol / 0.08 h / 0 °C

With hydrogenchloride; sodium tetrahydroborate; 2,2'-azobis(isobutyronitrile); dihydrogen peroxide; tri-n-butyl-tin hydride; sodium hydrogencarbonate; triethylamine; In tetrahydrofuran; methanol; dichloromethane; benzene;
DOI:10.1021/jo00102a025