2-[5-(dimethylamino)naphthalene-1-sulfonamido]ethyl 5-O-(2,3,5-tri-O-benzoyl-α-D-arabinofuranosyl)-2,3-di-O-tert-butyldimethylsilyl-α-D-arabinofuranoside

Base Information

Chemical Name:2-[5-(dimethylamino)naphthalene-1-sulfonamido]ethyl 5-O-(2,3,5-tri-O-benzoyl-α-D-arabinofuranosyl)-2,3-di-O-tert-butyldimethylsilyl-α-D-arabinofuranoside
CAS No.:330983-84-1
Molecular Formula:C₅₇H₇₄N₂O₁₄SSi₂
Molecular Weight:1099.46
Hs Code.:

2-[5-(dimethylamino)naphthalene-1-sulfonamido]ethyl 5-O-(2,3,5-tri-O-benzoyl-α-D-arabinofuranosyl)-2,3-di-O-tert-butyldimethylsilyl-α-D-arabinofuranoside

Synonyms:2-[5-(dimethylamino)naphthalene-1-sulfonamido]ethyl 5-O-(2,3,5-tri-O-benzoyl-α-D-arabinofuranosyl)-2,3-di-O-tert-butyldimethylsilyl-α-D-arabinofuranoside

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Chemical Property of 2-[5-(dimethylamino)naphthalene-1-sulfonamido]ethyl 5-O-(2,3,5-tri-O-benzoyl-α-D-arabinofuranosyl)-2,3-di-O-tert-butyldimethylsilyl-α-D-arabinofuranoside

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Technology Process of 2-[5-(dimethylamino)naphthalene-1-sulfonamido]ethyl 5-O-(2,3,5-tri-O-benzoyl-α-D-arabinofuranosyl)-2,3-di-O-tert-butyldimethylsilyl-α-D-arabinofuranoside

There total 10 articles about 2-[5-(dimethylamino)naphthalene-1-sulfonamido]ethyl 5-O-(2,3,5-tri-O-benzoyl-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: 95.0%

: 605-65-2
5-(dimethylamino)naphth-1-ylsulfonyl chloride

: 330983-83-0
2-aminoethyl 5-O-(2,3,5-tri-O-benzoyl-α-D-arabinofuranosyl)-2,3-di-O-tert-butyldimethylsilyl-α-D-arabinofuranoside

: 330983-84-1
2-[5-(dimethylamino)naphthalene-1-sulfonamido]ethyl 5-O-(2,3,5-tri-O-benzoyl-α-D-arabinofuranosyl)-2,3-di-O-tert-butyldimethylsilyl-α-D-arabinofuranoside

Guidance literature:: With 1-methyl-1H-imidazole; In dichloromethane; at 0 ℃; for 3h;
DOI:10.1016/S0040-4039(00)02161-4 DOI:10.1016/j.bmc.2007.04.012

Reference yield:

: 330983-77-2
2-ethylazido-α-D-arabinofuranoside

: 330983-84-1
2-[5-(dimethylamino)naphthalene-1-sulfonamido]ethyl 5-O-(2,3,5-tri-O-benzoyl-α-D-arabinofuranosyl)-2,3-di-O-tert-butyldimethylsilyl-α-D-arabinofuranoside

Guidance literature:: Multi-step reaction with 6 steps

1: 58 percent / pyridine / -78 - 20 °C

2: 81 percent / imidazole / dimethylformamide / 48 h / 87 °C

3: 93 percent / 7N NH₃/MeOH / 20 °C

4: 66 percent / BF₃*Et₂O / CH₂Cl₂ / 2 h / -20 °C

5: 87 percent / Ph₃P / benzene; H₂O / 6 h / 50 °C

6: 95 percent / N-methylimidazole / CH₂Cl₂ / 3 h / 0 °C

With pyridine; 1H-imidazole; 1-methyl-1H-imidazole; methanol; ammonium hydroxide; boron trifluoride diethyl etherate; triphenylphosphine; In dichloromethane; water; N,N-dimethyl-formamide; benzene;
DOI:10.1016/S0040-4039(00)02161-4

Reference yield:

: 330983-76-1
chloroethyl 2,3,5-tri-O-acetyl-α-D-arabinofuranoside

: 330983-84-1
2-[5-(dimethylamino)naphthalene-1-sulfonamido]ethyl 5-O-(2,3,5-tri-O-benzoyl-α-D-arabinofuranosyl)-2,3-di-O-tert-butyldimethylsilyl-α-D-arabinofuranoside

Guidance literature:: Multi-step reaction with 8 steps

1: NaN₃ / dimethylformamide / 6 h / 84 °C

2: 7N NH₃/MeOH / 20 °C

3: 58 percent / pyridine / -78 - 20 °C

4: 81 percent / imidazole / dimethylformamide / 48 h / 87 °C

5: 93 percent / 7N NH₃/MeOH / 20 °C

6: 66 percent / BF₃*Et₂O / CH₂Cl₂ / 2 h / -20 °C

7: 87 percent / Ph₃P / benzene; H₂O / 6 h / 50 °C

8: 95 percent / N-methylimidazole / CH₂Cl₂ / 3 h / 0 °C

With pyridine; 1H-imidazole; 1-methyl-1H-imidazole; methanol; ammonium hydroxide; sodium azide; boron trifluoride diethyl etherate; triphenylphosphine; In dichloromethane; water; N,N-dimethyl-formamide; benzene;
DOI:10.1016/S0040-4039(00)02161-4