tert-butyl (3R,4S)-4-benzyloxymethyloxy-3-(2-tert-butyldimethylsilyloxyethyl)-5-tetrahydropyranyloxypentanoate

Base Information

• Chemical Name: tert-butyl (3R,4S)-4-benzyloxymethyloxy-3-(2-tert-butyldimethylsilyloxyethyl)-5-tetrahydropyranyloxypentanoate
• CAS No.: 128322-03-2
• Molecular Formula: C₃₀H₅₂O₇Si
• Molecular Weight: 552.824
• Mol file: 128322-03-2.mol

Synonyms:tert-butyl (3R,4S)-4-benzyloxymethyloxy-3-(2-tert-butyldimethylsilyloxyethyl)-5-tetrahydropyranyloxypentanoate

Chemical Property of tert-butyl (3R,4S)-4-benzyloxymethyloxy-3-(2-tert-butyldimethylsilyloxyethyl)-5-tetrahydropyranyloxypentanoate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of tert-butyl (3R,4S)-4-benzyloxymethyloxy-3-(2-tert-butyldimethylsilyloxyethyl)-5-tetrahydropyranyloxypentanoate

There total 8 articles about tert-butyl (3R,4S)-4-benzyloxymethyloxy-3-(2-tert-butyldimethylsilyloxyethyl)-5-tetrahydropyranyloxypentanoate 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: 100.0%

Benzyloxymethyl chloride (3587-60-8) + tert-butyl (3R,4S)-3-(2-tert-butyldimethylsilyloxyethyl)-4-hydroxy-5-tetrahydropyranyloxypentanoate (128322-16-7) → tert-butyl (3R,4S)-4-benzyloxymethyloxy-3-(2-tert-butyldimethylsilyloxyethyl)-5-tetrahydropyranyloxypentanoate (128322-03-2)

Guidance literature:

With N-ethyl-N,N-diisopropylamine; In 1,2-dichloro-ethane; at 60 ℃; for 5h;

DOI:10.1248/cpb.40.1742

Reference yield:

(5S)-5-(hydroxymethyl)-5H-furan-2-one (78508-96-0) → tert-butyl (3R,4S)-4-benzyloxymethyloxy-3-(2-tert-butyldimethylsilyloxyethyl)-5-tetrahydropyranyloxypentanoate (128322-03-2)

Guidance literature:

Multi-step reaction with 6 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

With 1H-imidazole; sodium tetrahydroborate; camphor-10-sulfonic acid; diisobutylaluminium hydride; N-ethyl-N,N-diisopropylamine; lithium diisopropyl amide; In tetrahydrofuran; methanol; hexane; 1,2-dichloro-ethane;

DOI:10.1248/cpb.40.1742

Reference yield:

(4S)-4-hydroxy-5-tetrahydropyranyloxy-2-pentenoic acid γ-lactone (128387-70-2) → tert-butyl (3R,4S)-4-benzyloxymethyloxy-3-(2-tert-butyldimethylsilyloxyethyl)-5-tetrahydropyranyloxypentanoate (128322-03-2)

Guidance literature:

Multi-step reaction with 5 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

With 1H-imidazole; sodium tetrahydroborate; diisobutylaluminium hydride; N-ethyl-N,N-diisopropylamine; lithium diisopropyl amide; In tetrahydrofuran; methanol; hexane; 1,2-dichloro-ethane;

DOI:10.1248/cpb.40.1742

upstream raw materials:

Benzyloxymethyl chloride

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

3,4-dihydro-2H-pyran

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

Downstream raw materials:

(3S,4S)-4-Benzyloxymethoxy-3-[2-(tert-butyl-dimethyl-silanyloxy)-ethyl]-5-(tetrahydro-pyran-2-yloxy)-pentan-1-ol

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

{(5E,9E)-(3S,4S)-4-Benzyloxymethoxy-14-ethoxy-3-[2-(4-methoxy-benzyloxy)-ethyl]-6,10-dimethyl-pentadeca-5,9,14-trienyloxy}-tert-butyl-dimethyl-silane

(E)-(8S,9S)-8-Benzyloxymethoxy-11-(tert-butyl-dimethyl-silanyloxy)-9-[2-(4-methoxy-benzyloxy)-ethyl]-2,6-dimethyl-undeca-1,6-dien-3-ol