(2S,3S,4S)-4-(tert-butyldiphenylsilanyloxymethyl)-3,4-O-isopropylidenedioxy-2-methoxy-5-hexenal

Base Information

• Chemical Name: (2S,3S,4S)-4-(tert-butyldiphenylsilanyloxymethyl)-3,4-O-isopropylidenedioxy-2-methoxy-5-hexenal
• CAS No.: 870862-51-4
• Molecular Formula: C₂₇H₃₆O₅Si
• Molecular Weight: 468.665
• Mol file: 870862-51-4.mol

Synonyms:(2S,3S,4S)-4-(tert-butyldiphenylsilanyloxymethyl)-3,4-O-isopropylidenedioxy-2-methoxy-5-hexenal

Chemical Property of (2S,3S,4S)-4-(tert-butyldiphenylsilanyloxymethyl)-3,4-O-isopropylidenedioxy-2-methoxy-5-hexenal

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,3S,4S)-4-(tert-butyldiphenylsilanyloxymethyl)-3,4-O-isopropylidenedioxy-2-methoxy-5-hexenal

There total 6 articles about (2S,3S,4S)-4-(tert-butyldiphenylsilanyloxymethyl)-3,4-O-isopropylidenedioxy-2-methoxy-5-hexenal 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:

(2R,3R,4S,5S)-5-(tert-butyldiphenylsilanyloxymethyl)-4,5-O-isopropylidenedioxy-6-heptene-1,2-diol (870862-50-3) → (2S,3S,4S)-4-(tert-butyldiphenylsilanyloxymethyl)-3,4-O-isopropylidenedioxy-2-methoxy-5-hexenal (870862-51-4)

Guidance literature:

With sodium periodate; In tetrahydrofuran; water; at 20 ℃; for 1.5h;

DOI:10.1021/jo051686m

Reference yield:

(2S,3S,4R,5R)-2-C-(tert-butyldiphenylsilanyloxymethyl)-2,3:5,6-di-O-isopropylidene-D-mannofuranose (870862-47-8) → (2S,3S,4S)-4-(tert-butyldiphenylsilanyloxymethyl)-3,4-O-isopropylidenedioxy-2-methoxy-5-hexenal (870862-51-4)

Guidance literature:

Multi-step reaction with 4 steps

1.1: potassium tert-butoxide / toluene / 1 h / 105 °C

1.2: 97 percent / toluene / 2 h / 105 °C

2.1: 97 percent / NaH / various solvent(s); tetrahydrofuran / 4 h / 0 °C

3.1: 72 percent / acetic acid / H₂O / 4.5 h / 50 °C

4.1: NaIO₄ / tetrahydrofuran; H₂O / 1.5 h / 20 °C

With sodium periodate; potassium tert-butylate; sodium hydride; acetic acid; In tetrahydrofuran; water; toluene; 1.2: Wittig reaction;

DOI:10.1021/jo051686m

Reference yield:

(2R,3R,4S,5S)-5-(tert-butyldiphenylsilanyloxymethyl)-1,2:4,5-di-O-isopropylidenedioxy-6-hepten-3-ol (870862-48-9) → (2S,3S,4S)-4-(tert-butyldiphenylsilanyloxymethyl)-3,4-O-isopropylidenedioxy-2-methoxy-5-hexenal (870862-51-4)

Guidance literature:

Multi-step reaction with 3 steps

1: 97 percent / NaH / various solvent(s); tetrahydrofuran / 4 h / 0 °C

2: 72 percent / acetic acid / H₂O / 4.5 h / 50 °C

3: NaIO₄ / tetrahydrofuran; H₂O / 1.5 h / 20 °C

With sodium periodate; sodium hydride; acetic acid; In tetrahydrofuran; water;

DOI:10.1021/jo051686m

upstream raw materials:

(2R,3R,4S,5S)-5-(tert-butyldiphenylsilanyloxymethyl)-4,5-O-isopropylidenedioxy-6-heptene-1,2-diol

(2R,3R,4S,5S)-5-(tert-butyldiphenylsilanyloxymethyl)-1,2:4,5-di-O-isopropylidenedioxy-6-hepten-3-ol

(2R,3R,4S,5S)-5-(tert-butyldiphenylsilanyloxymethyl)-1,2:4,5-di-O-isopropylidenedioxy-3-methoxy-6-heptene

(2S,3S,4R,5R)-2-C-(tert-butyldiphenylsilanyloxymethyl)-2,3:5,6-di-O-isopropylidene-D-mannofuranose

Downstream raw materials:

(1S,2S,3R,4R)-1-hydroxymethyl-4-triethylsilyloxy-3-methoxy-1-cyclohexane-1,2-diol

(-)-ovalicin

(1S,2S,3R,4R)-1-(triethylsilyloxymethyl)-2,4-di(triethylsilyloxy)-3-methoxy-1-cyclohexanol

(1R,2R,3S,4S)-1-benzyloxy-4-(tert-butyldiphenylsilanyloxymethyl)-3,4-O-isopropylidenedioxy-2-methoxycyclohexane