(2S,3R,6S,8S)-6-((triethylsilyl)oxy)-8-((4S,5R,6S)-2,2,5-trimethyl-6-((S)-4-(trimethylsilyl)but-3-yn-2-yl)-1,3-dioxan-4-yl)-2-((4R,5R,6S)-2,2,5-trimethyl-6-((S,E)-4-methylhex-4-en-2-yl)-1,3-dioxan-4-yl)non-4-yn-3-yl (S)-3,3,3-trifluoro-2-methoxy-2-phenylpropanoate

Base Information

• Chemical Name: (2S,3R,6S,8S)-6-((triethylsilyl)oxy)-8-((4S,5R,6S)-2,2,5-trimethyl-6-((S)-4-(trimethylsilyl)but-3-yn-2-yl)-1,3-dioxan-4-yl)-2-((4R,5R,6S)-2,2,5-trimethyl-6-((S,E)-4-methylhex-4-en-2-yl)-1,3-dioxan-4-yl)non-4-yn-3-yl (S)-3,3,3-trifluoro-2-methoxy-2-phenylpropanoate
• CAS No.: 1638621-02-9
• Molecular Formula: C₅₃H₈₅F₃O₈Si₂
• Molecular Weight: 963.419

Synonyms:(2S,3R,6S,8S)-6-((triethylsilyl)oxy)-8-((4S,5R,6S)-2,2,5-trimethyl-6-((S)-4-(trimethylsilyl)but-3-yn-2-yl)-1,3-dioxan-4-yl)-2-((4R,5R,6S)-2,2,5-trimethyl-6-((S,E)-4-methylhex-4-en-2-yl)-1,3-dioxan-4-yl)non-4-yn-3-yl (S)-3,3,3-trifluoro-2-methoxy-2-phenylpropanoate

Chemical Property of (2S,3R,6S,8S)-6-((triethylsilyl)oxy)-8-((4S,5R,6S)-2,2,5-trimethyl-6-((S)-4-(trimethylsilyl)but-3-yn-2-yl)-1,3-dioxan-4-yl)-2-((4R,5R,6S)-2,2,5-trimethyl-6-((S,E)-4-methylhex-4-en-2-yl)-1,3-dioxan-4-yl)non-4-yn-3-yl (S)-3,3,3-trifluoro-2-methoxy-2-phenylpropanoate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
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Technology Process of (2S,3R,6S,8S)-6-((triethylsilyl)oxy)-8-((4S,5R,6S)-2,2,5-trimethyl-6-((S)-4-(trimethylsilyl)but-3-yn-2-yl)-1,3-dioxan-4-yl)-2-((4R,5R,6S)-2,2,5-trimethyl-6-((S,E)-4-methylhex-4-en-2-yl)-1,3-dioxan-4-yl)non-4-yn-3-yl (S)-3,3,3-trifluoro-2-methoxy-2-phenylpropanoate

There total 27 articles about (2S,3R,6S,8S)-6-((triethylsilyl)oxy)-8-((4S,5R,6S)-2,2,5-trimethyl-6-((S)-4-(trimethylsilyl)but-3-yn-2-yl)-1,3-dioxan-4-yl)-2-((4R,5R,6S)-2,2,5-trimethyl-6-((S,E)-4-methylhex-4-en-2-yl)-1,3-dioxan-4-yl)non-4-yn-3-yl (S)-3,3,3-trifluoro-2-methoxy-2-phenylpropanoate 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: 62.0%

(2R,3R,6S,8S)-6-((triethylsilyl)oxy)-8-((4S,5R,6S)-2,2,5-trimethyl-6-((S)-4-(trimethylsilyl)but-3-yn-2-yl)-1,3-dioxan-4-yl)-2-((4S,5R,6S)-2,2,5-trimethyl-6-((S,E)-4-methylhex-4-en-2-yl)-1,3-dioxan-4-yl)non-4-yn-3-ol (1638621-04-1) + (S)-Mosher acid (17257-71-5,20445-31-2,56135-03-6,81655-41-6) → (2S,3R,6S,8S)-6-((triethylsilyl)oxy)-8-((4S,5R,6S)-2,2,5-trimethyl-6-((S)-4-(trimethylsilyl)but-3-yn-2-yl)-1,3-dioxan-4-yl)-2-((4R,5R,6S)-2,2,5-trimethyl-6-((S,E)-4-methylhex-4-en-2-yl)-1,3-dioxan-4-yl)non-4-yn-3-yl (S)-3,3,3-trifluoro-2-methoxy-2-phenylpropanoate (1638621-02-9)

Guidance literature:

With dmap; dicyclohexyl-carbodiimide; In dichloromethane; at 20 ℃; for 16h; Inert atmosphere;

DOI:10.1002/anie.201402056

Reference yield:

(S)-methyl 3-((S)-2,2-dimethyl-1,3-dioxolan-4-yl)-2-methylpropanoate (1383002-64-9) → (2S,3R,6S,8S)-6-((triethylsilyl)oxy)-8-((4S,5R,6S)-2,2,5-trimethyl-6-((S)-4-(trimethylsilyl)but-3-yn-2-yl)-1,3-dioxan-4-yl)-2-((4R,5R,6S)-2,2,5-trimethyl-6-((S,E)-4-methylhex-4-en-2-yl)-1,3-dioxan-4-yl)non-4-yn-3-yl (S)-3,3,3-trifluoro-2-methoxy-2-phenylpropanoate (1638621-02-9)

Guidance literature:

Multi-step reaction with 14 steps

1.1: diisobutylaluminium hydride / dichloromethane / 0.5 h / -78 °C / Inert atmosphere

1.2: 16 h / 20 °C / Inert atmosphere

2.1: toluene / 16 h / -78 °C / Inert atmosphere; Molecular sieve

2.2: 2 h / 20 °C / Inert atmosphere

3.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 16 h / 0 - 20 °C / Inert atmosphere

3.2: -78 °C / Inert atmosphere

4.1: palladium diacetate; triphenylphosphine / tetrahydrofuran / 20 °C / Inert atmosphere

4.2: 1.5 h / -78 - 20 °C / Inert atmosphere

5.1: acetone / 1 h / -20 °C / 5171.62 Torr / Inert atmosphere; Flow reactor

6.1: sodium hydrogencarbonate; Dess-Martin periodane / dichloromethane / 1 h / 20 °C / Inert atmosphere

7.1: triphenylphosphine; carbon tetrabromide; triethylamine / dichloromethane / 0.67 h / -78 - 0 °C / Inert atmosphere

8.1: diisobutylaluminium hydride / dichloromethane / 0.5 h / 0 °C / Inert atmosphere

8.2: 16 h / 20 °C / Inert atmosphere

9.1: 2,6-dimethylpyridine; hydrogenchloride / dichloromethane; water / 0.33 h / 0 °C / Inert atmosphere; Flow reactor

10.1: n-butyllithium / tetrahydrofuran; hexane / 0.67 h / -78 - 20 °C / Inert atmosphere

11.1: n-butyllithium / tetrahydrofuran; hexane / 1.17 h / -78 - 20 °C / Inert atmosphere

11.2: 1 h / -78 - 20 °C / Inert atmosphere

12.1: manganese(IV) oxide / dichloromethane / 2 h / 20 °C / Inert atmosphere

13.1: (3aR)-1-methyl-3,3-diphenyl-tetrahydro-pyrrolo[1,2-c][1,3,2]oxazaborole; dimethylsulfide borane complex / tetrahydrofuran / 18 h / -78 - 20 °C / Inert atmosphere; Molecular sieve; Schlenk technique

14.1: dicyclohexyl-carbodiimide; dmap / dichloromethane / 16 h / 20 °C / Inert atmosphere

With 2,6-dimethylpyridine; hydrogenchloride; dmap; manganese(IV) oxide; n-butyllithium; carbon tetrabromide; dimethylsulfide borane complex; palladium diacetate; diisobutylaluminium hydride; sodium hydrogencarbonate; Dess-Martin periodane; triethylamine; N-ethyl-N,N-diisopropylamine; dicyclohexyl-carbodiimide; triphenylphosphine; (3aR)-1-methyl-3,3-diphenyl-tetrahydro-pyrrolo[1,2-c][1,3,2]oxazaborole; In tetrahydrofuran; hexane; dichloromethane; water; acetone; toluene;

DOI:10.1002/anie.201402056

Reference yield:

(S)-3-((S)-2,2-dimethyl-1,3-dioxolan-4-yl)-2-methylpropanal (1287211-21-5) → (2S,3R,6S,8S)-6-((triethylsilyl)oxy)-8-((4S,5R,6S)-2,2,5-trimethyl-6-((S)-4-(trimethylsilyl)but-3-yn-2-yl)-1,3-dioxan-4-yl)-2-((4R,5R,6S)-2,2,5-trimethyl-6-((S,E)-4-methylhex-4-en-2-yl)-1,3-dioxan-4-yl)non-4-yn-3-yl (S)-3,3,3-trifluoro-2-methoxy-2-phenylpropanoate (1638621-02-9)

Guidance literature:

Multi-step reaction with 13 steps

1.1: toluene / 16 h / -78 °C / Inert atmosphere; Molecular sieve

1.2: 2 h / 20 °C / Inert atmosphere

2.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 16 h / 0 - 20 °C / Inert atmosphere

2.2: -78 °C / Inert atmosphere

3.1: palladium diacetate; triphenylphosphine / tetrahydrofuran / 20 °C / Inert atmosphere

3.2: 1.5 h / -78 - 20 °C / Inert atmosphere

4.1: acetone / 1 h / -20 °C / 5171.62 Torr / Inert atmosphere; Flow reactor

5.1: sodium hydrogencarbonate; Dess-Martin periodane / dichloromethane / 1 h / 20 °C / Inert atmosphere

6.1: triphenylphosphine; carbon tetrabromide; triethylamine / dichloromethane / 0.67 h / -78 - 0 °C / Inert atmosphere

7.1: diisobutylaluminium hydride / dichloromethane / 0.5 h / 0 °C / Inert atmosphere

7.2: 16 h / 20 °C / Inert atmosphere

8.1: 2,6-dimethylpyridine; hydrogenchloride / dichloromethane; water / 0.33 h / 0 °C / Inert atmosphere; Flow reactor

9.1: n-butyllithium / tetrahydrofuran; hexane / 0.67 h / -78 - 20 °C / Inert atmosphere

10.1: n-butyllithium / tetrahydrofuran; hexane / 1.17 h / -78 - 20 °C / Inert atmosphere

10.2: 1 h / -78 - 20 °C / Inert atmosphere

11.1: manganese(IV) oxide / dichloromethane / 2 h / 20 °C / Inert atmosphere

12.1: (3aR)-1-methyl-3,3-diphenyl-tetrahydro-pyrrolo[1,2-c][1,3,2]oxazaborole; dimethylsulfide borane complex / tetrahydrofuran / 18 h / -78 - 20 °C / Inert atmosphere; Molecular sieve; Schlenk technique

13.1: dicyclohexyl-carbodiimide; dmap / dichloromethane / 16 h / 20 °C / Inert atmosphere

With 2,6-dimethylpyridine; hydrogenchloride; dmap; manganese(IV) oxide; n-butyllithium; carbon tetrabromide; dimethylsulfide borane complex; palladium diacetate; diisobutylaluminium hydride; sodium hydrogencarbonate; Dess-Martin periodane; triethylamine; N-ethyl-N,N-diisopropylamine; dicyclohexyl-carbodiimide; triphenylphosphine; (3aR)-1-methyl-3,3-diphenyl-tetrahydro-pyrrolo[1,2-c][1,3,2]oxazaborole; In tetrahydrofuran; hexane; dichloromethane; water; acetone; toluene;

DOI:10.1002/anie.201402056

upstream raw materials:

(4S,5R,6S)-4-((R)-but-3-en-2-yl)-6-((S)-1-((S)-2,2-dimethyl-1,3-dioxolan-4-yl)propan-2-yl)-2,2,5-trimethyl-1,3-dioxane

(R)-2-((4S,5R,6S)-6-((S)-1-((S)-2,2-dimethyl-1,3-dioxolan-4-yl)propan-2-yl)-2,2,5-trimethyl-1,3-dioxan-4-yl)propan-1-ol

tert-butyl((R)-2-((4S,5R,6S)-6-((S)-1-((S)-2,2-dimethyl-1,3-dioxolan-4-yl)propan-2-yl)-2,2,5-trimethyl-1,3-dioxan-4-yl)propoxy)dimethylsilane

(S)-3-((4S,5R,6S)-6-((R)-1-((tert-butyldimethylsilyl)oxy)propan-2-yl)-2,2,5-trimethyl-1,3-dioxan-4-yl)butanal

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