(1S,2R,4R,5S,7S,8S)-7-(tert-Butyl-dimethyl-silanyloxy)-8-hydroxy-5-{(S)-4-[(R)-3-hydroxy-1-(4-methoxy-benzyloxy)-propyl]-2,2-dimethyl-[1,3]dioxolan-4-yl}-2-methoxymethoxy-4,11,11-trimethyl-bicyclo[6.2.1]undecan-3-one

Base Information

• Chemical Name: (1S,2R,4R,5S,7S,8S)-7-(tert-Butyl-dimethyl-silanyloxy)-8-hydroxy-5-{(S)-4-[(R)-3-hydroxy-1-(4-methoxy-benzyloxy)-propyl]-2,2-dimethyl-[1,3]dioxolan-4-yl}-2-methoxymethoxy-4,11,11-trimethyl-bicyclo[6.2.1]undecan-3-one
• CAS No.: 171625-70-0
• Molecular Formula: C₃₈H₆₄O₁₀Si
• Molecular Weight: 709.006

Synonyms:

Chemical Property of (1S,2R,4R,5S,7S,8S)-7-(tert-Butyl-dimethyl-silanyloxy)-8-hydroxy-5-{(S)-4-[(R)-3-hydroxy-1-(4-methoxy-benzyloxy)-propyl]-2,2-dimethyl-[1,3]dioxolan-4-yl}-2-methoxymethoxy-4,11,11-trimethyl-bicyclo[6.2.1]undecan-3-one

Chemical Property:

Purity/Quality:

Safty Information:

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Useful:

Technology Process of (1S,2R,4R,5S,7S,8S)-7-(tert-Butyl-dimethyl-silanyloxy)-8-hydroxy-5-{(S)-4-[(R)-3-hydroxy-1-(4-methoxy-benzyloxy)-propyl]-2,2-dimethyl-[1,3]dioxolan-4-yl}-2-methoxymethoxy-4,11,11-trimethyl-bicyclo[6.2.1]undecan-3-one

There total 11 articles about (1S,2R,4R,5S,7S,8S)-7-(tert-Butyl-dimethyl-silanyloxy)-8-hydroxy-5-{(S)-4-[(R)-3-hydroxy-1-(4-methoxy-benzyloxy)-propyl]-2,2-dimethyl-[1,3]dioxolan-4-yl}-2-methoxymethoxy-4,11,11-trimethyl-bicyclo[6.2.1]undecan-3-one 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:

(S)-4-[(R)-1-(4-Methoxy-benzyloxy)-allyl]-2,2-dimethyl-[1,3]dioxolane-4-carbaldehyde (171625-65-3) → (1S,2R,4R,5S,7S,8S)-7-(tert-Butyl-dimethyl-silanyloxy)-8-hydroxy-5-{(S)-4-[(R)-3-hydroxy-1-(4-methoxy-benzyloxy)-propyl]-2,2-dimethyl-[1,3]dioxolan-4-yl}-2-methoxymethoxy-4,11,11-trimethyl-bicyclo[6.2.1]undecan-3-one (171625-70-0)

Guidance literature:

Multi-step reaction with 6 steps

1: 71 percent / NaN(TMS)2 / tetrahydrofuran / 1.5 h / -78 °C

2: 70 percent / t-BuLi / tetrahydrofuran; hexane / 1.) -78 deg C, 2 min, 2.) -78 deg C, 20 min

3: 1.) 18-crown-6, KN(SiMe₃)2 / 1.) toluene, -45 deg C, 25 min, 2.) -78 deg C, 1 h

4: 1.) OsO₄, pyridine, 2.) Na₂S₂O₄ / 1.) H₂O, -30 deg C, 1.5 h; room temp., 2.5 h, 2.) room temp., overnight

5: imidazole / dimethylformamide / 2 h

6: 1.) borane-THF, 2.3-dimethyl-2-butene, 2.) 2 M NaOH, 30percent H₂O₂ / 1.) THF, 0 deg C, 2 h, 2.) 15 min

With pyridine; 1H-imidazole; sodium hydroxide; osmium(VIII) oxide; sodium dithionite; 2,3-Dimethyl-2-butene; borane-THF; 18-crown-6 ether; dihydrogen peroxide; tert.-butyl lithium; sodium hexamethyldisilazane; potassium hexamethylsilazane; In tetrahydrofuran; hexane; N,N-dimethyl-formamide;

DOI:10.1021/jo00129a027

Reference yield:

(2S,3R,4R)-2-Diethoxymethyl-3-(4-methoxy-benzyloxy)-pentane-1,2,4,5-tetraol → (1S,2R,4R,5S,7S,8S)-7-(tert-Butyl-dimethyl-silanyloxy)-8-hydroxy-5-{(S)-4-[(R)-3-hydroxy-1-(4-methoxy-benzyloxy)-propyl]-2,2-dimethyl-[1,3]dioxolan-4-yl}-2-methoxymethoxy-4,11,11-trimethyl-bicyclo[6.2.1]undecan-3-one (171625-70-0)

Guidance literature:

Multi-step reaction with 9 steps

1: acetone / 2 h / Heating

2: 89 percent / (C₆H₅)3P, imidazole, I₂ / toluene; acetonitrile / 1 h / Heating

3: 95 percent / Zn / methanol / 1.5 h / Heating

4: 71 percent / NaN(TMS)2 / tetrahydrofuran / 1.5 h / -78 °C

5: 70 percent / t-BuLi / tetrahydrofuran; hexane / 1.) -78 deg C, 2 min, 2.) -78 deg C, 20 min

6: 1.) 18-crown-6, KN(SiMe₃)2 / 1.) toluene, -45 deg C, 25 min, 2.) -78 deg C, 1 h

7: 1.) OsO₄, pyridine, 2.) Na₂S₂O₄ / 1.) H₂O, -30 deg C, 1.5 h; room temp., 2.5 h, 2.) room temp., overnight

8: imidazole / dimethylformamide / 2 h

9: 1.) borane-THF, 2.3-dimethyl-2-butene, 2.) 2 M NaOH, 30percent H₂O₂ / 1.) THF, 0 deg C, 2 h, 2.) 15 min

With pyridine; 1H-imidazole; sodium hydroxide; osmium(VIII) oxide; sodium dithionite; 2,3-Dimethyl-2-butene; borane-THF; 18-crown-6 ether; dihydrogen peroxide; iodine; tert.-butyl lithium; sodium hexamethyldisilazane; potassium hexamethylsilazane; triphenylphosphine; zinc; In tetrahydrofuran; methanol; hexane; N,N-dimethyl-formamide; acetone; toluene; acetonitrile;

DOI:10.1021/jo00129a027

Reference yield:

(5S,8S,9R)-6-Ethoxy-8-(iodomethyl)-9-<(p-methoxybenzyl)oxy>-2,2-dimethyl-1,3,7-trioxaspiro<4.4>nonane → (1S,2R,4R,5S,7S,8S)-7-(tert-Butyl-dimethyl-silanyloxy)-8-hydroxy-5-{(S)-4-[(R)-3-hydroxy-1-(4-methoxy-benzyloxy)-propyl]-2,2-dimethyl-[1,3]dioxolan-4-yl}-2-methoxymethoxy-4,11,11-trimethyl-bicyclo[6.2.1]undecan-3-one (171625-70-0)

Guidance literature:

Multi-step reaction with 7 steps

1: 95 percent / Zn / methanol / 1.5 h / Heating

2: 71 percent / NaN(TMS)2 / tetrahydrofuran / 1.5 h / -78 °C

3: 70 percent / t-BuLi / tetrahydrofuran; hexane / 1.) -78 deg C, 2 min, 2.) -78 deg C, 20 min

4: 1.) 18-crown-6, KN(SiMe₃)2 / 1.) toluene, -45 deg C, 25 min, 2.) -78 deg C, 1 h

5: 1.) OsO₄, pyridine, 2.) Na₂S₂O₄ / 1.) H₂O, -30 deg C, 1.5 h; room temp., 2.5 h, 2.) room temp., overnight

6: imidazole / dimethylformamide / 2 h

7: 1.) borane-THF, 2.3-dimethyl-2-butene, 2.) 2 M NaOH, 30percent H₂O₂ / 1.) THF, 0 deg C, 2 h, 2.) 15 min

With pyridine; 1H-imidazole; sodium hydroxide; osmium(VIII) oxide; sodium dithionite; 2,3-Dimethyl-2-butene; borane-THF; 18-crown-6 ether; dihydrogen peroxide; tert.-butyl lithium; sodium hexamethyldisilazane; potassium hexamethylsilazane; zinc; In tetrahydrofuran; methanol; hexane; N,N-dimethyl-formamide;

DOI:10.1021/jo00129a027

upstream raw materials:

(1S,2R,4R,5S,7S,8S)-7-(tert-Butyl-dimethyl-silanyloxy)-8-hydroxy-5-{(S)-4-[(R)-1-(4-methoxy-benzyloxy)-allyl]-2,2-dimethyl-[1,3]dioxolan-4-yl}-2-methoxymethoxy-4,11,11-trimethyl-bicyclo[6.2.1]undecan-3-one

(S)-4-[(R)-1-(4-Methoxy-benzyloxy)-allyl]-2,2-dimethyl-[1,3]dioxolane-4-carbaldehyde

(S)-2-((R)-((R)-2,2-Dimethyl-1,3-dioxolan-4-yl)((p-methoxybenzyl)oxy)methyl)glycidaldehyde diethyl acetal

2-C-(Hydroxymethyl)-4,5-O-isopropylidene-3-O-(p-methoxybenzyl)-D-arabinose diethyl acetal

Downstream raw materials:

(R)-3-{(S)-4-[(1S,2S,4S,5R,7R,8S)-2-(tert-Butyl-dimethyl-silanyloxy)-1-hydroxy-7-methoxymethoxy-5,11,11-trimethyl-6-oxo-bicyclo[6.2.1]undec-4-yl]-2,2-dimethyl-[1,3]dioxolan-4-yl}-3-(4-methoxy-benzyloxy)-propionaldehyde

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