(E)-(4S,5R)-7-(tert-Butyl-diphenyl-silanyloxy)-5-hydroxy-4-methoxy-2-methyl-hept-2-enoic acid methyl ester

Base Information

Chemical Name:(E)-(4S,5R)-7-(tert-Butyl-diphenyl-silanyloxy)-5-hydroxy-4-methoxy-2-methyl-hept-2-enoic acid methyl ester
CAS No.:192931-97-8
Molecular Formula:C₂₆H₃₆O₅Si
Molecular Weight:456.654
Hs Code.:

Synonyms:(E)-(4S,5R)-7-(tert-Butyl-diphenyl-silanyloxy)-5-hydroxy-4-methoxy-2-methyl-hept-2-enoic acid methyl ester

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Chemical Property of (E)-(4S,5R)-7-(tert-Butyl-diphenyl-silanyloxy)-5-hydroxy-4-methoxy-2-methyl-hept-2-enoic acid methyl ester

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Technology Process of (E)-(4S,5R)-7-(tert-Butyl-diphenyl-silanyloxy)-5-hydroxy-4-methoxy-2-methyl-hept-2-enoic acid methyl ester

There total 6 articles about (E)-(4S,5R)-7-(tert-Butyl-diphenyl-silanyloxy)-5-hydroxy-4-methoxy-2-methyl-hept-2-enoic 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: 93.0%

: 58479-61-1
tert-butylchlorodiphenylsilane

: 192931-88-7
(E)-(4S,5R)-5,7-Dihydroxy-4-methoxy-2-methyl-hept-2-enoic acid methyl ester

: 192931-97-8
(E)-(4S,5R)-7-(tert-Butyl-diphenyl-silanyloxy)-5-hydroxy-4-methoxy-2-methyl-hept-2-enoic acid methyl ester

Guidance literature:: With dmap; TEA; In dichloromethane; Ambient temperature;
DOI:10.1016/S0040-4039(97)00925-8

Reference yield:

: 18968-50-8,29587-02-8,32166-85-1,36215-54-0,43138-65-4,65725-74-8,67816-77-7
1-[6-methoxy-2,2-dimethyl-(3aR,5R,6R,6aR)-perhydrofuro-[2,3-d][1,3]dioxol-5-yl]-(1R)-ethane-1,2-diol

: 192931-97-8
(E)-(4S,5R)-7-(tert-Butyl-diphenyl-silanyloxy)-5-hydroxy-4-methoxy-2-methyl-hept-2-enoic acid methyl ester

Guidance literature:: Multi-step reaction with 6 steps

1: TEA / CH₂Cl₂ / 0.5 h / -30 - -20 °C

2: NaI / butan-2-one / 9 h / 100 °C

3: 1.) 9-BBN; 2.) 30percent H₂O₂, 3N NaOH / 1.) THF, -40 deg C to r.t., overnight; 2.) 60-70 deg C, 2 h

4: Dowex 50x2-200 resin / H₂O / 1 h / 100 °C

5: 1.) NaIO₄; 3.) K₂CO₃ / 1.) Me₂CO, H₂O, r.t., 2 h; 2.) MeCN, 100-110 deg C, 20 h; 3.) MeOH, r.t., 4 h

6: 93 percent / DMAP, TEA / CH₂Cl₂ / Ambient temperature

With dmap; sodium hydroxide; sodium periodate; 9-borabicyclo[3.3.1]nonane dimer; Dowex 50x2-200 resin; TEA; dihydrogen peroxide; potassium carbonate; sodium iodide; In dichloromethane; water; butanone;
DOI:10.1016/S0040-4039(97)00925-8

Reference yield:

: 32166-82-8
Methanesulfonic acid (R)-2-methanesulfonyloxy-1-((3aR,5S,6R,6aR)-6-methoxy-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-ethyl ester

: 192931-97-8
(E)-(4S,5R)-7-(tert-Butyl-diphenyl-silanyloxy)-5-hydroxy-4-methoxy-2-methyl-hept-2-enoic acid methyl ester

Guidance literature:: Multi-step reaction with 5 steps

1: NaI / butan-2-one / 9 h / 100 °C

2: 1.) 9-BBN; 2.) 30percent H₂O₂, 3N NaOH / 1.) THF, -40 deg C to r.t., overnight; 2.) 60-70 deg C, 2 h

3: Dowex 50x2-200 resin / H₂O / 1 h / 100 °C

4: 1.) NaIO₄; 3.) K₂CO₃ / 1.) Me₂CO, H₂O, r.t., 2 h; 2.) MeCN, 100-110 deg C, 20 h; 3.) MeOH, r.t., 4 h

5: 93 percent / DMAP, TEA / CH₂Cl₂ / Ambient temperature

With dmap; sodium hydroxide; sodium periodate; 9-borabicyclo[3.3.1]nonane dimer; Dowex 50x2-200 resin; TEA; dihydrogen peroxide; potassium carbonate; sodium iodide; In dichloromethane; water; butanone;
DOI:10.1016/S0040-4039(97)00925-8