octyl 5-(5-deoxy-5-N-di(cyclohexylmethyl)amino-α-D-arabinofuranosyl)-2,3-di-O-tert-butyldimethylsilyl-α-D-arabinofuranoside

Base Information

• Chemical Name: octyl 5-(5-deoxy-5-N-di(cyclohexylmethyl)amino-α-D-arabinofuranosyl)-2,3-di-O-tert-butyldimethylsilyl-α-D-arabinofuranoside
• CAS No.: 651706-64-8
• Molecular Formula: C₄₄H₈₇NO₈Si₂
• Molecular Weight: 814.348
• Mol file: 651706-64-8.mol

Synonyms:octyl 5-(5-deoxy-5-N-di(cyclohexylmethyl)amino-α-D-arabinofuranosyl)-2,3-di-O-tert-butyldimethylsilyl-α-D-arabinofuranoside

Chemical Property of octyl 5-(5-deoxy-5-N-di(cyclohexylmethyl)amino-α-D-arabinofuranosyl)-2,3-di-O-tert-butyldimethylsilyl-α-D-arabinofuranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of octyl 5-(5-deoxy-5-N-di(cyclohexylmethyl)amino-α-D-arabinofuranosyl)-2,3-di-O-tert-butyldimethylsilyl-α-D-arabinofuranoside

There total 5 articles about octyl 5-(5-deoxy-5-N-di(cyclohexylmethyl)amino-α-D-arabinofuranosyl)-2,3-di-O-tert-butyldimethylsilyl-α-D-arabinofuranoside 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: 87.0%

cyclohexanecarbaldehyde (2043-61-0) + octyl 5-O-(5-deoxy-5-azido-α-D-arabinofuranosyl)-2,3-di-O-tert-butyldimethylsilyl-α-D-arabinofuranoside (651706-61-5) → octyl 5-(5-deoxy-5-N-di(cyclohexylmethyl)amino-α-D-arabinofuranosyl)-2,3-di-O-tert-butyldimethylsilyl-α-D-arabinofuranoside (651706-64-8)

Guidance literature:

With hydrogen; palladium on activated charcoal; In methanol; at 20 ℃; for 1h;

DOI:10.1016/j.tet.2003.10.054

Reference yield:

octyl α-D-arabinofranose tetraacetate (352438-36-9) → octyl 5-(5-deoxy-5-N-di(cyclohexylmethyl)amino-α-D-arabinofuranosyl)-2,3-di-O-tert-butyldimethylsilyl-α-D-arabinofuranoside (651706-64-8)

Guidance literature:

Multi-step reaction with 5 steps

1: 96 percent / imidazole / dimethylformamide / 6 h / 20 °C

2: 74 percent / TFA / H₂O / 4 h / -4 °C

3: 69 percent / N-iodosuccinimide; Sn(OTf)2 / CH₂Cl₂ / 0.5 h / 20 °C

4: 74 percent / NH₃ / methanol / 6 h / 20 °C

5: 87 percent / H₂ / Pd/C / methanol / 1 h / 20 °C

With 1H-imidazole; N-iodo-succinimide; tin(II) trifluoromethanesulfonate; ammonia; hydrogen; trifluoroacetic acid; palladium on activated charcoal; In methanol; dichloromethane; water; N,N-dimethyl-formamide;

DOI:10.1016/j.tet.2003.10.054

Reference yield:

octyl 2,3-di-O-tert-butyldimethylsilyl-α-D-arabinofuranoside (651706-59-1) → octyl 5-(5-deoxy-5-N-di(cyclohexylmethyl)amino-α-D-arabinofuranosyl)-2,3-di-O-tert-butyldimethylsilyl-α-D-arabinofuranoside (651706-64-8)

Guidance literature:

Multi-step reaction with 3 steps

1: 69 percent / N-iodosuccinimide; Sn(OTf)2 / CH₂Cl₂ / 0.5 h / 20 °C

2: 74 percent / NH₃ / methanol / 6 h / 20 °C

3: 87 percent / H₂ / Pd/C / methanol / 1 h / 20 °C

With N-iodo-succinimide; tin(II) trifluoromethanesulfonate; ammonia; hydrogen; palladium on activated charcoal; In methanol; dichloromethane;

DOI:10.1016/j.tet.2003.10.054

upstream raw materials:

cyclohexanecarbaldehyde

octyl 5-O-(5-deoxy-5-azido-α-D-arabinofuranosyl)-2,3-di-O-tert-butyldimethylsilyl-α-D-arabinofuranoside

octyl α-D-arabinofranose tetraacetate

octyl 2,3-di-O-tert-butyldimethylsilyl-α-D-arabinofuranoside