2,5-di-O-benzyl-3,4-bis-O-(tert-butyldimethylsilyl)-L-ido-hexodialdose

Base Information

• Chemical Name: 2,5-di-O-benzyl-3,4-bis-O-(tert-butyldimethylsilyl)-L-ido-hexodialdose
• CAS No.: 700864-03-5
• Molecular Formula: C₃₂H₅₀O₆Si₂
• Molecular Weight: 586.916
• Mol file: 700864-03-5.mol

Synonyms:2,5-di-O-benzyl-3,4-bis-O-(tert-butyldimethylsilyl)-L-ido-hexodialdose

Chemical Property of 2,5-di-O-benzyl-3,4-bis-O-(tert-butyldimethylsilyl)-L-ido-hexodialdose

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2,5-di-O-benzyl-3,4-bis-O-(tert-butyldimethylsilyl)-L-ido-hexodialdose

There total 11 articles about 2,5-di-O-benzyl-3,4-bis-O-(tert-butyldimethylsilyl)-L-ido-hexodialdose 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: 82.0%

2,5-di-O-benzyl-3,4-bis-O-(tert-butyldimethylsilyl)-D-chiro-inositol (700864-02-4) → 2,5-di-O-benzyl-3,4-bis-O-(tert-butyldimethylsilyl)-L-ido-hexodialdose (700864-03-5)

Guidance literature:

With sodium periodate; In acetonitrile; at 65 ℃; for 6h;

DOI:10.1039/b316506j

Reference yield:

3,4-di-O-allyl-2,5-di-O-benzyl-D-chiro-inositol (110550-25-9) → 2,5-di-O-benzyl-3,4-bis-O-(tert-butyldimethylsilyl)-L-ido-hexodialdose (700864-03-5)

Guidance literature:

Multi-step reaction with 5 steps

1.1: 53 percent / 4-(dimethylamino)pyridine; pyridine / 0.67 h / 0 - 20 °C

2.1: (1,5-cyclooctadiene)bis(PPh₂Me)Ir(I)*PF₆ / tetrahydrofuran / 1.5 h / 20 °C

2.2: 60 percent / AcCl / tetrahydrofuran; methanol / 0.5 h / 20 °C

3.1: imidazole / dimethylformamide / 18 h / 85 °C

3.2: 60 percent / 2,6-lutidine / dimethylformamide / 18 h / 65 °C

4.1: 83 percent / NaOMe / methanol / 18 h / 20 °C / pH 12

5.1: 82 percent / aq. NaIO₄ / acetonitrile / 6 h / 65 °C

With pyridine; 1H-imidazole; dmap; sodium periodate; sodium methylate; (1,5-cyclooctadiene)[bis(methyldiphenylphosphine)]iridium(I) hexafluorophosphate; In tetrahydrofuran; methanol; N,N-dimethyl-formamide; acetonitrile;

DOI:10.1039/b316506j

Reference yield:

1,2:5,6-bis-O-(1-methylethylidene)-D-chiro-inositol (40617-60-5) → 2,5-di-O-benzyl-3,4-bis-O-(tert-butyldimethylsilyl)-L-ido-hexodialdose (700864-03-5)

Guidance literature:

Multi-step reaction with 8 steps

1.1: NaH / dimethylformamide / 0.5 h / ice bath cooling

1.2: 80 percent / dimethylformamide / 2 h / 20 °C

2.1: 99 percent / aq. HCl / methanol / 1 h / 20 °C

3.1: (Bu₃Sn)2O / toluene / 1.5 h / 110 °C

3.2: 53 percent / Bu₄NBr / toluene / 2 h / 110 °C

4.1: 53 percent / 4-(dimethylamino)pyridine; pyridine / 0.67 h / 0 - 20 °C

5.1: (1,5-cyclooctadiene)bis(PPh₂Me)Ir(I)*PF₆ / tetrahydrofuran / 1.5 h / 20 °C

5.2: 60 percent / AcCl / tetrahydrofuran; methanol / 0.5 h / 20 °C

6.1: imidazole / dimethylformamide / 18 h / 85 °C

6.2: 60 percent / 2,6-lutidine / dimethylformamide / 18 h / 65 °C

7.1: 83 percent / NaOMe / methanol / 18 h / 20 °C / pH 12

8.1: 82 percent / aq. NaIO₄ / acetonitrile / 6 h / 65 °C

With pyridine; 1H-imidazole; hydrogenchloride; dmap; sodium periodate; sodium methylate; sodium hydride; bis(tri-n-butyltin)oxide; (1,5-cyclooctadiene)[bis(methyldiphenylphosphine)]iridium(I) hexafluorophosphate; In tetrahydrofuran; methanol; N,N-dimethyl-formamide; toluene; acetonitrile;

DOI:10.1039/b316506j

upstream raw materials:

2,5-di-O-benzyl-3,4-bis-O-(tert-butyldimethylsilyl)-D-chiro-inositol

t-butyldimethylsiyl triflate

benzyl bromide

tert-butyldimethylsilyl chloride

Downstream raw materials:

N-benzyl-3,6-di-O-benzyl-4,5-bis-O-(tert-butyldimethylsilyl)-L-ido-3,4,5,6-tetrahydoxyazepane

N-benzyl-3,6-di-O-benzyl-L-ido-3,4,5,6-tetrahydroxyazepane