2D-(1,5/1,2,3,4)-1-O-acetyl-1,5-anhydro-4-O-[(tert-butyl)dimethylsilyl]-2,3-O-isopropylidenecyclopentane-1,1,2,3,4,5-hexol

Base Information

• Chemical Name: 2D-(1,5/1,2,3,4)-1-O-acetyl-1,5-anhydro-4-O-[(tert-butyl)dimethylsilyl]-2,3-O-isopropylidenecyclopentane-1,1,2,3,4,5-hexol
• CAS No.: 560132-74-3
• Molecular Formula: C₁₆H₂₈O₆Si
• Molecular Weight: 344.48
• Mol file: 560132-74-3.mol

Synonyms:2D-(1,5/1,2,3,4)-1-O-acetyl-1,5-anhydro-4-O-[(tert-butyl)dimethylsilyl]-2,3-O-isopropylidenecyclopentane-1,1,2,3,4,5-hexol

Chemical Property of 2D-(1,5/1,2,3,4)-1-O-acetyl-1,5-anhydro-4-O-[(tert-butyl)dimethylsilyl]-2,3-O-isopropylidenecyclopentane-1,1,2,3,4,5-hexol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2D-(1,5/1,2,3,4)-1-O-acetyl-1,5-anhydro-4-O-[(tert-butyl)dimethylsilyl]-2,3-O-isopropylidenecyclopentane-1,1,2,3,4,5-hexol

There total 1 articles about 2D-(1,5/1,2,3,4)-1-O-acetyl-1,5-anhydro-4-O-[(tert-butyl)dimethylsilyl]-2,3-O-isopropylidenecyclopentane-1,1,2,3,4,5-hexol 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: 50.0%

5-amino-4-O-[(tert-butyl)dimethylsilyl]-5-deoxy-2,3-O-isopropylidene-{[(4-methylphenyl)sulfonyl]amino}-D-ribono-1,5-lactam → 2D-(2,3,4/0)-4-O-[(tert-butyl)dimethylsilyl]-5-diazo-2,3-O-isopropylidene-2,3,4-trihydroxycyclopentanone + 2D-(1,5/1,2,3,4)-1-O-acetyl-1,5-anhydro-4-O-[(tert-butyl)dimethylsilyl]-2,3-O-isopropylidenecyclopentane-1,1,2,3,4,5-hexol (560132-74-3) + (5R)-5-O-acetyl-5-amino-4-O-[(tert-butyl)dimethylsilyl]-2,3-O-isopropylidene-N-{[(4-methylphenyl)sulfonyl]amino}-D-ribono-1,5-lactam

Guidance literature:

With lead(IV) acetate; In dichloromethane; toluene; at 23 ℃; for 2h;

DOI:10.1002/hlca.200490218

Reference yield:

2D-(1,5/1,2,3,4)-1-O-acetyl-1,5-anhydro-4-O-[(tert-butyl)dimethylsilyl]-2,3-O-isopropylidenecyclopentane-1,1,2,3,4,5-hexol (560132-74-3) → 1D-(1,2,3,4/5)-1-O-benzoyl-4-O-[(tert-butyl)dimethylsilyl]-2,3-O-isopropylidenecyclopentane-1,2,3,4,5-pentol

Guidance literature:

Multi-step reaction with 2 steps

1: 80.5 percent / LiAlH₄ / tetrahydrofuran / 2 h / 0 °C

2: 67 percent / TMEDA / CH₂Cl₂ / 30 h / -40 °C

With lithium aluminium tetrahydride; N,N,N,N,-tetramethylethylenediamine; In tetrahydrofuran; dichloromethane;

DOI:10.1002/hlca.200490217

Reference yield:

2D-(1,5/1,2,3,4)-1-O-acetyl-1,5-anhydro-4-O-[(tert-butyl)dimethylsilyl]-2,3-O-isopropylidenecyclopentane-1,1,2,3,4,5-hexol (560132-74-3) → mannostatin A (102822-56-0)

Guidance literature:

Multi-step reaction with 8 steps

1.1: 80.5 percent / LiAlH₄ / tetrahydrofuran / 2 h / 0 °C

2.1: 91 percent / pyridine / CH₂Cl₂ / 6 h / -60 °C

3.1: 99 percent / pyridine / CH₂Cl₂ / 5 h / 0 - 23 °C

4.1: 94 percent / 15-crown-15 / tetrahydrofuran / 2 h / 23 °C

5.1: 99 percent / TBAF / tetrahydrofuran / 2.5 h / -30 °C

6.1: 100 percent / DBU / CH₂Cl₂ / 1 h / 23 °C

7.1: 33 percent / EtN(i-Pr)2 / xylene / 24 h / 110 °C

8.1: HCl; water / methanol / 3 h / 23 °C

8.2: 81.5 percent / Amberlite IR-120 (H+) / toluene

With pyridine; hydrogenchloride; lithium aluminium tetrahydride; 15-crown-15; tetrabutyl ammonium fluoride; water; 1,8-diazabicyclo[5.4.0]undec-7-ene; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; methanol; dichloromethane; xylene;

DOI:10.1002/hlca.200490217

Downstream raw materials:

mannostatin A

1D-(1,2,3,4/5)-2,3,4-trihydroxy-5-(methylsulfanyl)cyclopentane-1-ammonium chloride