Benzyl-((S)-2-benzyloxy-1-{(4S,5S)-5-[(Z)-(R)-1-(tert-butyl-dimethyl-silanyloxy)-tetradec-2-enyl]-2,2-dimethyl-[1,3]dioxolan-4-yl}-ethyl)-amine

Base Information

• Chemical Name: Benzyl-((S)-2-benzyloxy-1-{(4S,5S)-5-[(Z)-(R)-1-(tert-butyl-dimethyl-silanyloxy)-tetradec-2-enyl]-2,2-dimethyl-[1,3]dioxolan-4-yl}-ethyl)-amine
• CAS No.: 241824-97-5
• Molecular Formula: C₄₁H₆₇NO₄Si
• Molecular Weight: 666.073

Synonyms:Benzyl-((S)-2-benzyloxy-1-{(4S,5S)-5-[(Z)-(R)-1-(tert-butyl-dimethyl-silanyloxy)-tetradec-2-enyl]-2,2-dimethyl-[1,3]dioxolan-4-yl}-ethyl)-amine

Chemical Property of Benzyl-((S)-2-benzyloxy-1-{(4S,5S)-5-[(Z)-(R)-1-(tert-butyl-dimethyl-silanyloxy)-tetradec-2-enyl]-2,2-dimethyl-[1,3]dioxolan-4-yl}-ethyl)-amine

Chemical Property:

Purity/Quality:

Safty Information:

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Technology Process of Benzyl-((S)-2-benzyloxy-1-{(4S,5S)-5-[(Z)-(R)-1-(tert-butyl-dimethyl-silanyloxy)-tetradec-2-enyl]-2,2-dimethyl-[1,3]dioxolan-4-yl}-ethyl)-amine

There total 15 articles about Benzyl-((S)-2-benzyloxy-1-{(4S,5S)-5-[(Z)-(R)-1-(tert-butyl-dimethyl-silanyloxy)-tetradec-2-enyl]-2,2-dimethyl-[1,3]dioxolan-4-yl}-ethyl)-amine 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:

(4R,5S)-diethyl 2,2-dimethyl-1,3-dioxolane-4,5-dicarboxylate (56543-05-6) → Benzyl-((S)-2-benzyloxy-1-{(4S,5S)-5-[(Z)-(R)-1-(tert-butyl-dimethyl-silanyloxy)-tetradec-2-enyl]-2,2-dimethyl-[1,3]dioxolan-4-yl}-ethyl)-amine (241824-97-5)

Guidance literature:

Multi-step reaction with 15 steps

1.1: 84 percent / LiAlH₄ / tetrahydrofuran

2.1: 75 percent / Et₃N / CH₂Cl₂

3.1: 93 percent / Lipase Amano PS; aq. phosphate buffer / acetone / 5 h / 20 °C

4.1: PPTS / CH₂Cl₂

5.1: K₂CO₃; MeOH

6.1: KHMDS / tetrahydrofuran

7.1: PPTs

9.1: tetrahydrofuran / -78 - 0 °C

10.1: 95 percent / imidazole / dimethylformamide

11.1: 99 percent / H₂; quinoline / Pd/BaSO₄ / methanol

12.1: 86 percent / Ca; NH₃

13.1: 93 percent / oxalyl chloride; DMSO; Et₃N / CH₂Cl₂

14.1: 100 percent / diethyl ether

15.1: n-BuLi; SnCl₂; LiBr / tetrahydrofuran; hexane / 1 h / -78 °C

15.2: BF₃*Et₂O / tetrahydrofuran / -78 °C

With 1H-imidazole; quinoline; methanol; lithium aluminium tetrahydride; n-butyllithium; phosphate buffer; oxalyl dichloride; Lipase Amano PS; ammonia; hydrogen; pyridinium p-toluenesulfonate; potassium hexamethylsilazane; calcium; potassium carbonate; dimethyl sulfoxide; triethylamine; tin(ll) chloride; lithium bromide; Pd-BaSO₄; pyridinium p-toluenesulfonate; In tetrahydrofuran; methanol; diethyl ether; hexane; dichloromethane; N,N-dimethyl-formamide; acetone; 1.1: Reduction / 2.1: Acylation / 3.1: Hydrolysis / 4.1: Etherification / 5.1: Substitution / 6.1: Etherification / 7.1: Substitution / 8.1: Swern oxidation / 9.1: Substitution / 10.1: Etherification / 11.1: Catalytic hydrogenation / 12.1: Substitution / 13.1: Oxidation / 14.1: Addition / 15.1: Metallation / 15.2: Addition;

DOI:10.1039/a902386k

Reference yield:

(2S,3R)-4-benzyloxy-2,3-(propane-2,2-dioxy)-1-butanol (502481-96-1) → Benzyl-((S)-2-benzyloxy-1-{(4S,5S)-5-[(Z)-(R)-1-(tert-butyl-dimethyl-silanyloxy)-tetradec-2-enyl]-2,2-dimethyl-[1,3]dioxolan-4-yl}-ethyl)-amine (241824-97-5)

Guidance literature:

Multi-step reaction with 8 steps

2.1: tetrahydrofuran / -78 - 0 °C

3.1: 95 percent / imidazole / dimethylformamide

4.1: 99 percent / H₂; quinoline / Pd/BaSO₄ / methanol

5.1: 86 percent / Ca; NH₃

6.1: 93 percent / oxalyl chloride; DMSO; Et₃N / CH₂Cl₂

7.1: 100 percent / diethyl ether

8.1: n-BuLi; SnCl₂; LiBr / tetrahydrofuran; hexane / 1 h / -78 °C

8.2: BF₃*Et₂O / tetrahydrofuran / -78 °C

With 1H-imidazole; quinoline; n-butyllithium; oxalyl dichloride; ammonia; hydrogen; calcium; dimethyl sulfoxide; triethylamine; tin(ll) chloride; lithium bromide; Pd-BaSO₄; In tetrahydrofuran; methanol; diethyl ether; hexane; dichloromethane; N,N-dimethyl-formamide; 1.1: Swern oxidation / 2.1: Substitution / 3.1: Etherification / 4.1: Catalytic hydrogenation / 5.1: Substitution / 6.1: Oxidation / 7.1: Addition / 8.1: Metallation / 8.2: Addition;

DOI:10.1039/a902386k

Reference yield:

((4R,5S)-5-Hydroxymethyl-2,2-dimethyl-[1,3]dioxolan-4-yl)-methanol (55904-12-6) → Benzyl-((S)-2-benzyloxy-1-{(4S,5S)-5-[(Z)-(R)-1-(tert-butyl-dimethyl-silanyloxy)-tetradec-2-enyl]-2,2-dimethyl-[1,3]dioxolan-4-yl}-ethyl)-amine (241824-97-5)

Guidance literature:

Multi-step reaction with 14 steps

1.1: 75 percent / Et₃N / CH₂Cl₂

2.1: 93 percent / Lipase Amano PS; aq. phosphate buffer / acetone / 5 h / 20 °C

3.1: PPTS / CH₂Cl₂

4.1: K₂CO₃; MeOH

5.1: KHMDS / tetrahydrofuran

6.1: PPTs

8.1: tetrahydrofuran / -78 - 0 °C

9.1: 95 percent / imidazole / dimethylformamide

10.1: 99 percent / H₂; quinoline / Pd/BaSO₄ / methanol

11.1: 86 percent / Ca; NH₃

12.1: 93 percent / oxalyl chloride; DMSO; Et₃N / CH₂Cl₂

13.1: 100 percent / diethyl ether

14.1: n-BuLi; SnCl₂; LiBr / tetrahydrofuran; hexane / 1 h / -78 °C

14.2: BF₃*Et₂O / tetrahydrofuran / -78 °C

With 1H-imidazole; quinoline; methanol; n-butyllithium; phosphate buffer; oxalyl dichloride; Lipase Amano PS; ammonia; hydrogen; pyridinium p-toluenesulfonate; potassium hexamethylsilazane; calcium; potassium carbonate; dimethyl sulfoxide; triethylamine; tin(ll) chloride; lithium bromide; Pd-BaSO₄; pyridinium p-toluenesulfonate; In tetrahydrofuran; methanol; diethyl ether; hexane; dichloromethane; N,N-dimethyl-formamide; acetone; 1.1: Acylation / 2.1: Hydrolysis / 3.1: Etherification / 4.1: Substitution / 5.1: Etherification / 6.1: Substitution / 7.1: Swern oxidation / 8.1: Substitution / 9.1: Etherification / 10.1: Catalytic hydrogenation / 11.1: Substitution / 12.1: Oxidation / 13.1: Addition / 14.1: Metallation / 14.2: Addition;

DOI:10.1039/a902386k

upstream raw materials:

Benzyloxymethyl chloride

Benzyl-[1-{(4S,5S)-5-[(Z)-(R)-1-(tert-butyl-dimethyl-silanyloxy)-tetradec-2-enyl]-2,2-dimethyl-[1,3]dioxolan-4-yl}-meth-(E)-ylidene]-amine

((4R,5S)-5-Hydroxymethyl-2,2-dimethyl-[1,3]dioxolan-4-yl)-methanol

(4R,5S)-diethyl 2,2-dimethyl-1,3-dioxolane-4,5-dicarboxylate

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