[(R)-1-((4S,5S)-5-Benzyloxymethyl-2,2-dimethyl-[1,3]dioxolan-4-yl)-tetradec-2-ynyloxy]-tert-butyl-dimethyl-silane

Base Information

• Chemical Name: [(R)-1-((4S,5S)-5-Benzyloxymethyl-2,2-dimethyl-[1,3]dioxolan-4-yl)-tetradec-2-ynyloxy]-tert-butyl-dimethyl-silane
• CAS No.: 241824-83-9
• Molecular Formula: C₃₃H₅₆O₄Si
• Molecular Weight: 544.891

Synonyms:[(R)-1-((4S,5S)-5-Benzyloxymethyl-2,2-dimethyl-[1,3]dioxolan-4-yl)-tetradec-2-ynyloxy]-tert-butyl-dimethyl-silane

Chemical Property of [(R)-1-((4S,5S)-5-Benzyloxymethyl-2,2-dimethyl-[1,3]dioxolan-4-yl)-tetradec-2-ynyloxy]-tert-butyl-dimethyl-silane

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of [(R)-1-((4S,5S)-5-Benzyloxymethyl-2,2-dimethyl-[1,3]dioxolan-4-yl)-tetradec-2-ynyloxy]-tert-butyl-dimethyl-silane

There total 10 articles about [(R)-1-((4S,5S)-5-Benzyloxymethyl-2,2-dimethyl-[1,3]dioxolan-4-yl)-tetradec-2-ynyloxy]-tert-butyl-dimethyl-silane 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: 95.0%

tert-butyldimethylsilyl chloride (18162-48-6) + (R)-1-((4R,5S)-5-Benzyloxymethyl-2,2-dimethyl-[1,3]dioxolan-4-yl)-tetradec-2-yn-1-ol (241824-81-7) → [(R)-1-((4S,5S)-5-Benzyloxymethyl-2,2-dimethyl-[1,3]dioxolan-4-yl)-tetradec-2-ynyloxy]-tert-butyl-dimethyl-silane (241824-83-9)

Guidance literature:

With 1H-imidazole; In N,N-dimethyl-formamide;

DOI:10.1039/a902386k

Reference yield:

(4R,5S)-diethyl 2,2-dimethyl-1,3-dioxolane-4,5-dicarboxylate (56543-05-6) → [(R)-1-((4S,5S)-5-Benzyloxymethyl-2,2-dimethyl-[1,3]dioxolan-4-yl)-tetradec-2-ynyloxy]-tert-butyl-dimethyl-silane (241824-83-9)

Guidance literature:

Multi-step reaction with 10 steps

1: 84 percent / LiAlH₄ / tetrahydrofuran

2: 75 percent / Et₃N / CH₂Cl₂

3: 93 percent / Lipase Amano PS; aq. phosphate buffer / acetone / 5 h / 20 °C

4: PPTS / CH₂Cl₂

5: K₂CO₃; MeOH

6: KHMDS / tetrahydrofuran

7: PPTs

9: tetrahydrofuran / -78 - 0 °C

10: 95 percent / imidazole / dimethylformamide

With 1H-imidazole; methanol; lithium aluminium tetrahydride; phosphate buffer; Lipase Amano PS; pyridinium p-toluenesulfonate; potassium hexamethylsilazane; potassium carbonate; triethylamine; pyridinium p-toluenesulfonate; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide; acetone; 1: Reduction / 2: Acylation / 3: Hydrolysis / 4: Etherification / 5: Substitution / 6: Etherification / 7: Substitution / 8: Swern oxidation / 9: Substitution / 10: Etherification;

DOI:10.1039/a902386k

Reference yield:

((4R,5S)-5-Hydroxymethyl-2,2-dimethyl-[1,3]dioxolan-4-yl)-methanol (55904-12-6) → [(R)-1-((4S,5S)-5-Benzyloxymethyl-2,2-dimethyl-[1,3]dioxolan-4-yl)-tetradec-2-ynyloxy]-tert-butyl-dimethyl-silane (241824-83-9)

Guidance literature:

Multi-step reaction with 9 steps

1: 75 percent / Et₃N / CH₂Cl₂

2: 93 percent / Lipase Amano PS; aq. phosphate buffer / acetone / 5 h / 20 °C

3: PPTS / CH₂Cl₂

4: K₂CO₃; MeOH

5: KHMDS / tetrahydrofuran

6: PPTs

8: tetrahydrofuran / -78 - 0 °C

9: 95 percent / imidazole / dimethylformamide

With 1H-imidazole; methanol; phosphate buffer; Lipase Amano PS; pyridinium p-toluenesulfonate; potassium hexamethylsilazane; potassium carbonate; triethylamine; pyridinium p-toluenesulfonate; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide; acetone; 1: Acylation / 2: Hydrolysis / 3: Etherification / 4: Substitution / 5: Etherification / 6: Substitution / 7: Swern oxidation / 8: Substitution / 9: Etherification;

DOI:10.1039/a902386k

upstream raw materials:

tert-butyldimethylsilyl chloride

(R)-1-((4R,5S)-5-Benzyloxymethyl-2,2-dimethyl-[1,3]dioxolan-4-yl)-tetradec-2-yn-1-ol

((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

Downstream raw materials:

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

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

[(Z)-(R)-1-((4S,5S)-5-Benzyloxymethyl-2,2-dimethyl-[1,3]dioxolan-4-yl)-tetradec-2-enyloxy]-tert-butyl-dimethyl-silane

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