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
Hs Code.:

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

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

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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%

: 2043-61-0
cyclohexanecarbaldehyde

: 651706-61-5
octyl 5-O-(5-deoxy-5-azido-α-D-arabinofuranosyl)-2,3-di-O-tert-butyldimethylsilyl-α-D-arabinofuranoside

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

Guidance literature:: With hydrogen; palladium on activated charcoal; In methanol; at 20 ℃; for 1h;
DOI:10.1016/j.tet.2003.10.054

Reference yield:

: 352438-36-9
octyl α-D-arabinofranose tetraacetate

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

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:

: 651706-59-1
octyl 2,3-di-O-tert-butyldimethylsilyl-α-D-arabinofuranoside

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

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