(S)-4-{(4S,5R)-5-[(1S,2S)-3-(4-methoxybenzyloxy)-1-(tert-butyldimethylsilanyloxy)-2-methylpropyl]-2,2-dimethyl-1,3-dioxolan-4-yl}-4-methoxybutan-1-ol

Base Information

• Chemical Name: (S)-4-{(4S,5R)-5-[(1S,2S)-3-(4-methoxybenzyloxy)-1-(tert-butyldimethylsilanyloxy)-2-methylpropyl]-2,2-dimethyl-1,3-dioxolan-4-yl}-4-methoxybutan-1-ol
• CAS No.: 866022-13-1
• Molecular Formula: C₂₈H₅₀O₇Si
• Molecular Weight: 526.786

Synonyms:(S)-4-{(4S,5R)-5-[(1S,2S)-3-(4-methoxybenzyloxy)-1-(tert-butyldimethylsilanyloxy)-2-methylpropyl]-2,2-dimethyl-1,3-dioxolan-4-yl}-4-methoxybutan-1-ol

Chemical Property of (S)-4-{(4S,5R)-5-[(1S,2S)-3-(4-methoxybenzyloxy)-1-(tert-butyldimethylsilanyloxy)-2-methylpropyl]-2,2-dimethyl-1,3-dioxolan-4-yl}-4-methoxybutan-1-ol

Chemical Property:

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Technology Process of (S)-4-{(4S,5R)-5-[(1S,2S)-3-(4-methoxybenzyloxy)-1-(tert-butyldimethylsilanyloxy)-2-methylpropyl]-2,2-dimethyl-1,3-dioxolan-4-yl}-4-methoxybutan-1-ol

There total 13 articles about (S)-4-{(4S,5R)-5-[(1S,2S)-3-(4-methoxybenzyloxy)-1-(tert-butyldimethylsilanyloxy)-2-methylpropyl]-2,2-dimethyl-1,3-dioxolan-4-yl}-4-methoxybutan-1-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:

(4S,5S)-5-((S)-1-methoxybut-3-enyl)-2,2-dimethyl-1,3-dioxolane-4-carbaldehyde (866021-71-8) → (S)-4-{(4S,5R)-5-[(1S,2S)-3-(4-methoxybenzyloxy)-1-(tert-butyldimethylsilanyloxy)-2-methylpropyl]-2,2-dimethyl-1,3-dioxolan-4-yl}-4-methoxybutan-1-ol (866022-13-1)

Guidance literature:

Multi-step reaction with 9 steps

1.1: c-Hex₂BCl; Et₃N / diethyl ether / 0 °C

1.2: -78 °C

1.3: 79 percent / aq. H₂O₂

2.1: 2,6-lutidine / CH₂Cl₂

3.1: K₂CO₃ / methanol

4.1: NaBH₄

5.1: NaIO₄

6.1: NaBH₄

7.1: PPTS / CH₂Cl₂

8.1: tetrahydrofuran

9.1: aq. H₂O₂; NaOH

With 2,6-dimethylpyridine; sodium hydroxide; sodium tetrahydroborate; sodium periodate; dicyclohexylboron chloride; dihydrogen peroxide; pyridinium p-toluenesulfonate; potassium carbonate; triethylamine; In tetrahydrofuran; methanol; diethyl ether; dichloromethane;

DOI:10.1021/ol051405x

Reference yield:

(S)-1-((4S,5S)-5-(((tert-butyldimethylsilyl)oxy)methyl)-2,2-dimethyl-1,3-dioxolan-4-yl)but-3-en-1-ol (866022-02-8) → (S)-4-{(4S,5R)-5-[(1S,2S)-3-(4-methoxybenzyloxy)-1-(tert-butyldimethylsilanyloxy)-2-methylpropyl]-2,2-dimethyl-1,3-dioxolan-4-yl}-4-methoxybutan-1-ol (866022-13-1)

Guidance literature:

Multi-step reaction with 12 steps

1.1: NaH / tetrahydrofuran

2.1: TBAF / tetrahydrofuran / 0 °C

3.1: Dess-Martin periodinane; NaHCO₃ / CH₂Cl₂

4.1: c-Hex₂BCl; Et₃N / diethyl ether / 0 °C

4.2: -78 °C

4.3: 79 percent / aq. H₂O₂

5.1: 2,6-lutidine / CH₂Cl₂

6.1: K₂CO₃ / methanol

7.1: NaBH₄

8.1: NaIO₄

9.1: NaBH₄

10.1: PPTS / CH₂Cl₂

11.1: tetrahydrofuran

12.1: aq. H₂O₂; NaOH

With 2,6-dimethylpyridine; sodium hydroxide; sodium tetrahydroborate; sodium periodate; dicyclohexylboron chloride; tetrabutyl ammonium fluoride; dihydrogen peroxide; pyridinium p-toluenesulfonate; sodium hydride; sodium hydrogencarbonate; potassium carbonate; Dess-Martin periodane; triethylamine; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; 3.1: Dess-Martin oxidation;

DOI:10.1021/ol051405x

Reference yield:

tert-butyl-[(4S,5S)-5-((S)-1-methoxybut-3-enyl)-2,2-dimethyl-1,3-dioxolan-4-ylmethoxy]dimethylsilane (866022-05-1) → (S)-4-{(4S,5R)-5-[(1S,2S)-3-(4-methoxybenzyloxy)-1-(tert-butyldimethylsilanyloxy)-2-methylpropyl]-2,2-dimethyl-1,3-dioxolan-4-yl}-4-methoxybutan-1-ol (866022-13-1)

Guidance literature:

Multi-step reaction with 11 steps

1.1: TBAF / tetrahydrofuran / 0 °C

2.1: Dess-Martin periodinane; NaHCO₃ / CH₂Cl₂

3.1: c-Hex₂BCl; Et₃N / diethyl ether / 0 °C

3.2: -78 °C

3.3: 79 percent / aq. H₂O₂

4.1: 2,6-lutidine / CH₂Cl₂

5.1: K₂CO₃ / methanol

6.1: NaBH₄

7.1: NaIO₄

8.1: NaBH₄

9.1: PPTS / CH₂Cl₂

10.1: tetrahydrofuran

11.1: aq. H₂O₂; NaOH

With 2,6-dimethylpyridine; sodium hydroxide; sodium tetrahydroborate; sodium periodate; dicyclohexylboron chloride; tetrabutyl ammonium fluoride; dihydrogen peroxide; pyridinium p-toluenesulfonate; sodium hydrogencarbonate; potassium carbonate; Dess-Martin periodane; triethylamine; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; 2.1: Dess-Martin oxidation;

DOI:10.1021/ol051405x

upstream raw materials:

(4S,5S)-5-((S)-1-methoxybut-3-enyl)-2,2-dimethyl-1,3-dioxolane-4-carbaldehyde

(S)-1-((4S,5S)-5-(((tert-butyldimethylsilyl)oxy)methyl)-2,2-dimethyl-1,3-dioxolan-4-yl)but-3-en-1-ol

tert-butyl-[(4S,5S)-5-((S)-1-methoxybut-3-enyl)-2,2-dimethyl-1,3-dioxolan-4-ylmethoxy]dimethylsilane

(2S,3S)-3-(tert-butyldimethylsilanyloxy)-3-[(4R,5S)-5-((S)-1-methoxybut-3-enyl)-2,2-dimethyl-1,3-dioxolan-4-yl]-2-methylpropan-1-ol

Downstream raw materials:

C₆₀H₁₀₈O₁₂Si₃

C₆₀H₁₀₈O₁₂Si₃

C₆₀H₁₁₀O₁₂Si₃

C₆₀H₁₁₀O₁₂Si₃

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