(2S,3R,4S)-4-(tert-butyldimethylsiloxy)-hex-5-yn-2,3-diol 2-(para-nitrobenzoate ester)

Base Information

• Chemical Name: (2S,3R,4S)-4-(tert-butyldimethylsiloxy)-hex-5-yn-2,3-diol 2-(para-nitrobenzoate ester)
• CAS No.: 476469-46-2
• Molecular Formula: C₁₉H₂₇NO₆Si
• Molecular Weight: 393.512
• Mol file: 476469-46-2.mol

Synonyms:(2S,3R,4S)-4-(tert-butyldimethylsiloxy)-hex-5-yn-2,3-diol 2-(para-nitrobenzoate ester)

Chemical Property of (2S,3R,4S)-4-(tert-butyldimethylsiloxy)-hex-5-yn-2,3-diol 2-(para-nitrobenzoate ester)

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,3R,4S)-4-(tert-butyldimethylsiloxy)-hex-5-yn-2,3-diol 2-(para-nitrobenzoate ester)

There total 5 articles about (2S,3R,4S)-4-(tert-butyldimethylsiloxy)-hex-5-yn-2,3-diol 2-(para-nitrobenzoate ester) 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:

tert-butyldimethylsilyl chloride (18162-48-6) + (2S,3R,4S)-hex-5-yn-2,3,4-triol 2-(para-nitrobenzoate ester) → (2S,3R,4S)-4-(tert-butyldimethylsiloxy)-hex-5-yn-2,3-diol 2-(para-nitrobenzoate ester) (476469-46-2)

Guidance literature:

With 1H-imidazole; In dichloromethane; at 20 ℃; for 16h;

DOI:10.1021/ol026886o

Reference yield:

(E)-1-Trimethylsilanyl-hex-4-en-1-yn-3-one → (2S,3R,4S)-4-(tert-butyldimethylsiloxy)-hex-5-yn-2,3-diol 2-(para-nitrobenzoate ester) (476469-46-2)

Guidance literature:

Multi-step reaction with 4 steps

1.1: NaBH₄; CeCl₃ / CH₂Cl₂; methanol / -78 °C

1.2: 42 percent / L-(+)-DIPT; t-BuOOH / Ti(O-i-Pr)4 / CH₂Cl₂; decane / 5.5 h / -25 °C

2.1: HF*pyridine / tetrahydrofuran / 12 h / 0 °C

3.1: 453 mg / imidazole / CH₂Cl₂ / 16 h / 20 °C

With 1H-imidazole; sodium tetrahydroborate; cerium(III) chloride; pyridine hydrogenfluoride; In tetrahydrofuran; methanol; dichloromethane; 1.1: Sharpless epoxidation;

DOI:10.1021/ol026886o

Reference yield:

(3S,4R,5S)-1-(trimethylsilyl)-4,5-epoxyhex-1-yn-3-ol (279684-66-1) → (2S,3R,4S)-4-(tert-butyldimethylsiloxy)-hex-5-yn-2,3-diol 2-(para-nitrobenzoate ester) (476469-46-2)

Guidance literature:

Multi-step reaction with 3 steps

1: HF*pyridine / tetrahydrofuran / 12 h / 0 °C

2: 453 mg / imidazole / CH₂Cl₂ / 16 h / 20 °C

With 1H-imidazole; pyridine hydrogenfluoride; In tetrahydrofuran; dichloromethane;

DOI:10.1021/ol026886o

upstream raw materials:

tert-butyldimethylsilyl chloride

(3S,4R,5S)-1-(trimethylsilyl)-4,5-epoxyhex-1-yn-3-ol

(2S,3R,4S)-3,4-bis-(tert-butyldimethylsiloxy)-hex-5-yn-2-ol p-nitrobenzoate ester

4-nitro-benzoic acid

Downstream raw materials:

4-Nitro-benzoic acid (1S,2R,3S)-3-(tert-butyl-dimethyl-silanyloxy)-2-[(2S,4S,5R,6S)-4-(tert-butyl-dimethyl-silanyloxy)-5-((2S,4S,5R,6S)-4,5-diacetoxy-6-methyl-tetrahydro-pyran-2-yloxy)-6-methyl-tetrahydro-pyran-2-yloxy]-1-methyl-pent-4-ynyl ester

4-Nitro-benzoic acid (1S,2R,3S)-2-[(2S,4S,5R,6S)-4-acetoxy-5-((2S,4S,5R,6S)-4,5-diacetoxy-6-methyl-tetrahydro-pyran-2-yloxy)-6-methyl-tetrahydro-pyran-2-yloxy]-3-(tert-butyl-dimethyl-silanyloxy)-1-methyl-pent-4-ynyl ester

4-Nitro-benzoic acid (1S,2R,3S)-2-[(2S,4S,5R,6S)-4,5-bis-(tert-butyl-dimethyl-silanyloxy)-6-methyl-tetrahydro-pyran-2-yloxy]-3-(tert-butyl-dimethyl-silanyloxy)-1-methyl-pent-4-ynyl ester

4-Nitro-benzoic acid (1S,2R,3S)-3-(tert-butyl-dimethyl-silanyloxy)-2-((2S,4S,5R,6S)-4,5-diacetoxy-6-methyl-tetrahydro-pyran-2-yloxy)-1-methyl-pent-4-ynyl ester