(2S,3S)-2-benzyloxymethyloxy-5-tert-butyldimethylsilyloxy-3-<2-(p-methoxyphenyl)methyloxyethyl>pentan-1-al

Base Information

• Chemical Name: (2S,3S)-2-benzyloxymethyloxy-5-tert-butyldimethylsilyloxy-3-<2-(p-methoxyphenyl)methyloxyethyl>pentan-1-al
• CAS No.: 128322-04-3
• Molecular Formula: C₂₉H₄₄O₆Si
• Molecular Weight: 516.75
• Mol file: 128322-04-3.mol

Synonyms:(2S,3S)-2-benzyloxymethyloxy-5-tert-butyldimethylsilyloxy-3-<2-(p-methoxyphenyl)methyloxyethyl>pentan-1-al

Chemical Property of (2S,3S)-2-benzyloxymethyloxy-5-tert-butyldimethylsilyloxy-3-<2-(p-methoxyphenyl)methyloxyethyl>pentan-1-al

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,3S)-2-benzyloxymethyloxy-5-tert-butyldimethylsilyloxy-3-<2-(p-methoxyphenyl)methyloxyethyl>pentan-1-al

There total 10 articles about (2S,3S)-2-benzyloxymethyloxy-5-tert-butyldimethylsilyloxy-3-<2-(p-methoxyphenyl)methyloxyethyl>pentan-1-al 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: 99.0%

(2S,3S)-2-O-benzyloxymethyloxy-5-O-tert-butyldimethylsilyl-3-<2-(p-methoxyphenyl)methyloxyethyl>pentane-1,2,5-triol (128322-19-0) → (2S,3S)-2-benzyloxymethyloxy-5-tert-butyldimethylsilyloxy-3-<2-(p-methoxyphenyl)methyloxyethyl>pentan-1-al (128322-04-3)

Guidance literature:

With oxalyl dichloride; dimethyl sulfoxide; triethylamine; In dichloromethane; at -70 ℃; for 0.333333h;

DOI:10.1248/cpb.40.1742

Reference yield:

(5S)-5-(hydroxymethyl)-5H-furan-2-one (78508-96-0) → (2S,3S)-2-benzyloxymethyloxy-5-tert-butyldimethylsilyloxy-3-<2-(p-methoxyphenyl)methyloxyethyl>pentan-1-al (128322-04-3)

Guidance literature:

Multi-step reaction with 10 steps

1: 95 percent / CSA / tetrahydrofuran / 15 h / 10 °C

2: 1.) LDA / 1.) hexane, THF, -78 deg C, 40 min, 2.) hexane, THF, -78 deg C, 30 min

3: 53 percent / diisobutylaluminum hydride (DIBAH) / hexane; tetrahydrofuran / 0.5 h

4: 66 percent / NaBH₄ / methanol / 0.33 h / 0 °C

5: 88 percent / imidazole / tetrahydrofuran / 20 h / Ambient temperature

6: 100 percent / diisopropylethylamine / 1,2-dichloro-ethane / 5 h / 60 °C

7: LAH / diethyl ether / 0.5 h / 0 °C

8: NaH / tetrahydrofuran; dimethylformamide / 5 h / Ambient temperature

9: MgBr / diethyl ether / 7 h / Ambient temperature

10: 99 percent / DMSO, oxalyl chloride, Et₃N / CH₂Cl₂ / 0.33 h / -70 °C

With 1H-imidazole; sodium tetrahydroborate; lithium aluminium tetrahydride; oxalyl dichloride; camphor-10-sulfonic acid; sodium hydride; diisobutylaluminium hydride; dimethyl sulfoxide; triethylamine; N-ethyl-N,N-diisopropylamine; magnesium bromide; lithium diisopropyl amide; In tetrahydrofuran; methanol; diethyl ether; hexane; dichloromethane; 1,2-dichloro-ethane; N,N-dimethyl-formamide;

DOI:10.1248/cpb.40.1742

Reference yield:

(4S)-4-hydroxy-5-tetrahydropyranyloxy-2-pentenoic acid γ-lactone (128387-70-2) → (2S,3S)-2-benzyloxymethyloxy-5-tert-butyldimethylsilyloxy-3-<2-(p-methoxyphenyl)methyloxyethyl>pentan-1-al (128322-04-3)

Guidance literature:

Multi-step reaction with 9 steps

1: 1.) LDA / 1.) hexane, THF, -78 deg C, 40 min, 2.) hexane, THF, -78 deg C, 30 min

2: 53 percent / diisobutylaluminum hydride (DIBAH) / hexane; tetrahydrofuran / 0.5 h

3: 66 percent / NaBH₄ / methanol / 0.33 h / 0 °C

4: 88 percent / imidazole / tetrahydrofuran / 20 h / Ambient temperature

5: 100 percent / diisopropylethylamine / 1,2-dichloro-ethane / 5 h / 60 °C

6: LAH / diethyl ether / 0.5 h / 0 °C

7: NaH / tetrahydrofuran; dimethylformamide / 5 h / Ambient temperature

8: MgBr / diethyl ether / 7 h / Ambient temperature

9: 99 percent / DMSO, oxalyl chloride, Et₃N / CH₂Cl₂ / 0.33 h / -70 °C

With 1H-imidazole; sodium tetrahydroborate; lithium aluminium tetrahydride; oxalyl dichloride; sodium hydride; diisobutylaluminium hydride; dimethyl sulfoxide; triethylamine; N-ethyl-N,N-diisopropylamine; magnesium bromide; lithium diisopropyl amide; In tetrahydrofuran; methanol; diethyl ether; hexane; dichloromethane; 1,2-dichloro-ethane; N,N-dimethyl-formamide;

DOI:10.1248/cpb.40.1742

upstream raw materials:

(2S,3S)-2-O-benzyloxymethyloxy-5-O-tert-butyldimethylsilyl-3-<2-(p-methoxyphenyl)methyloxyethyl>pentane-1,2,5-triol

(5S)-5-(hydroxymethyl)-5H-furan-2-one

(4S)-4-hydroxy-5-tetrahydropyranyloxy-2-pentenoic acid γ-lactone

tert-butyl (3R,4S)-3-(2-hydroxy)ethyl-4-hydroxy-5-tetrahydropyranyloxypentanoate

Downstream raw materials:

(4S,5S)-4-Benzyloxymethoxy-7-(tert-butyl-dimethyl-silanyloxy)-5-[2-(4-methoxy-benzyloxy)-ethyl]-2-methyl-hept-1-en-3-ol

(6E,10E)-(12S,13S)-12-Benzyloxymethoxy-15-(tert-butyl-dimethyl-silanyloxy)-13-(2-hydroxy-ethyl)-6,10-dimethyl-pentadeca-6,10-dien-2-one

(3R,4S,5E,9E)-4-benzyloxymethyloxy-3-(2-tert-butyldimethylsilyloxyethyl)-6,10-dimethyl-14-oxo-5,9-pentadecadienoic acid

(4E,8E)-(10S,11S)-10-Benzyloxymethoxy-13-(tert-butyl-dimethyl-silanyloxy)-11-[2-(4-methoxy-benzyloxy)-ethyl]-4,8-dimethyl-trideca-4,8-dien-1-ol