(E)-(4S,7S,8R)-8-Benzyloxy-10-(tert-butyl-diphenyl-silanyloxy)-7-methoxy-5-methyl-deca-1,5-dien-4-ol

Base Information

Chemical Name:(E)-(4S,7S,8R)-8-Benzyloxy-10-(tert-butyl-diphenyl-silanyloxy)-7-methoxy-5-methyl-deca-1,5-dien-4-ol
CAS No.:192931-85-4
Molecular Formula:C₃₅H₄₆O₄Si
Molecular Weight:558.833
Hs Code.:

Synonyms:(E)-(4S,7S,8R)-8-Benzyloxy-10-(tert-butyl-diphenyl-silanyloxy)-7-methoxy-5-methyl-deca-1,5-dien-4-ol

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Chemical Property of (E)-(4S,7S,8R)-8-Benzyloxy-10-(tert-butyl-diphenyl-silanyloxy)-7-methoxy-5-methyl-deca-1,5-dien-4-ol

Chemical Property:

Purity/Quality:

Safty Information:

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Hazard Codes:

MSDS Files:

Useful:

Technology Process of (E)-(4S,7S,8R)-8-Benzyloxy-10-(tert-butyl-diphenyl-silanyloxy)-7-methoxy-5-methyl-deca-1,5-dien-4-ol

There total 9 articles about (E)-(4S,7S,8R)-8-Benzyloxy-10-(tert-butyl-diphenyl-silanyloxy)-7-methoxy-5-methyl-deca-1,5-dien-4-ol 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:

: 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

: 192931-85-4
(E)-(4S,7S,8R)-8-Benzyloxy-10-(tert-butyl-diphenyl-silanyloxy)-7-methoxy-5-methyl-deca-1,5-dien-4-ol

Guidance literature:: Multi-step reaction with 10 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

7: CF₃SO₃H / cyclohexane; CH₂Cl₂ / Ambient temperature

8: DIBALH / toluene / 1.5 h / -78 °C

9: 90 percent / MnO₂ / CCl₄ / Ambient temperature

10: tetrahydrofuran / 1 h / -78 - 0 °C

With dmap; manganese(IV) oxide; sodium hydroxide; sodium periodate; 9-borabicyclo[3.3.1]nonane dimer; trifluorormethanesulfonic acid; Dowex 50x2-200 resin; TEA; dihydrogen peroxide; diisobutylaluminium hydride; potassium carbonate; sodium iodide; In tetrahydrofuran; tetrachloromethane; dichloromethane; cyclohexane; water; toluene; 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

: 192931-85-4
(E)-(4S,7S,8R)-8-Benzyloxy-10-(tert-butyl-diphenyl-silanyloxy)-7-methoxy-5-methyl-deca-1,5-dien-4-ol

Guidance literature:: Multi-step reaction with 9 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

6: CF₃SO₃H / cyclohexane; CH₂Cl₂ / Ambient temperature

7: DIBALH / toluene / 1.5 h / -78 °C

8: 90 percent / MnO₂ / CCl₄ / Ambient temperature

9: tetrahydrofuran / 1 h / -78 - 0 °C

With dmap; manganese(IV) oxide; sodium hydroxide; sodium periodate; 9-borabicyclo[3.3.1]nonane dimer; trifluorormethanesulfonic acid; Dowex 50x2-200 resin; TEA; dihydrogen peroxide; diisobutylaluminium hydride; potassium carbonate; sodium iodide; In tetrahydrofuran; tetrachloromethane; dichloromethane; cyclohexane; water; toluene; butanone;
DOI:10.1016/S0040-4039(97)00925-8

Reference yield:

: (3R,4S,5R)-5-(2-Hydroxy-ethyl)-4-methoxy-tetrahydro-furan-2,3-diol

: 192931-85-4
(E)-(4S,7S,8R)-8-Benzyloxy-10-(tert-butyl-diphenyl-silanyloxy)-7-methoxy-5-methyl-deca-1,5-dien-4-ol

Guidance literature:: Multi-step reaction with 6 steps

1: 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

2: 93 percent / DMAP, TEA / CH₂Cl₂ / Ambient temperature

3: CF₃SO₃H / cyclohexane; CH₂Cl₂ / Ambient temperature

4: DIBALH / toluene / 1.5 h / -78 °C

5: 90 percent / MnO₂ / CCl₄ / Ambient temperature

6: tetrahydrofuran / 1 h / -78 - 0 °C

With dmap; manganese(IV) oxide; sodium periodate; trifluorormethanesulfonic acid; TEA; diisobutylaluminium hydride; potassium carbonate; In tetrahydrofuran; tetrachloromethane; dichloromethane; cyclohexane; toluene;
DOI:10.1016/S0040-4039(97)00925-8