methyl 4-azido-3-O-benzyl-6-O-t-butyldiphenylsilyl-2,4-dideoxy-β-D-arabino-hexoside

Base Information

Chemical Name:methyl 4-azido-3-O-benzyl-6-O-t-butyldiphenylsilyl-2,4-dideoxy-β-D-arabino-hexoside
CAS No.:151183-18-5
Molecular Formula:C₃₀H₃₇N₃O₄Si
Molecular Weight:531.727
Hs Code.:

Synonyms:methyl 4-azido-3-O-benzyl-6-O-t-butyldiphenylsilyl-2,4-dideoxy-β-D-arabino-hexoside

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Chemical Property of methyl 4-azido-3-O-benzyl-6-O-t-butyldiphenylsilyl-2,4-dideoxy-β-D-arabino-hexoside

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Technology Process of methyl 4-azido-3-O-benzyl-6-O-t-butyldiphenylsilyl-2,4-dideoxy-β-D-arabino-hexoside

There total 16 articles about methyl 4-azido-3-O-benzyl-6-O-t-butyldiphenylsilyl-2,4-dideoxy-β-D-arabino-hexoside 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: 88.0%

: 151130-26-6
methyl 3-O-benzyl-6-O-t-butyldiphenylsilyl-2-deoxy-4-O-methylsulfonyl-β-D-lyxo-hexoside

: 151183-18-5
methyl 4-azido-3-O-benzyl-6-O-t-butyldiphenylsilyl-2,4-dideoxy-β-D-arabino-hexoside

Guidance literature:: With sodium azide; In N,N-dimethyl-formamide; at 130 ℃;

Reference yield:

: 1824-94-8
methyl beta-D-galactopyranoside

: 151183-18-5
methyl 4-azido-3-O-benzyl-6-O-t-butyldiphenylsilyl-2,4-dideoxy-β-D-arabino-hexoside

Guidance literature:: Multi-step reaction with 12 steps

1: 85 percent / camphor-10-sulfonic acid / 48 h

2: 1.) NaH / 1.) DMF, 0.5 h, 2.) DMF, -10 deg C, 1 h

3: dimethylformamide / 1 h / -10 °C

4: camphor-10-sulfonic acid / methanol; H₂O / 0.5 h

5: 92 percent / tributylstannane / toluene / 14 h / Heating

6: 82 percent / 50percent aq. AcOH / 8 h

7: 76 percent / camphor-10-sulfonic acid / CHCl₃ / 2 h / Heating

8: 93 percent / NaH / dimethylformamide / 2 h

9: 98 percent / 50percent aq. AcOH / CH₂Cl₂ / 6 h

10: ethyldiisopropylamine / dimethylformamide

11: 81 percent / pyridine / CH₂Cl₂ / 3 h

12: 88 percent / NaN₃ / dimethylformamide / 130 °C

With pyridine; sodium azide; camphor-10-sulfonic acid; tri-n-butyl-tin hydride; sodium hydride; acetic acid; N-ethyl-N,N-diisopropylamine; In methanol; dichloromethane; chloroform; water; N,N-dimethyl-formamide; toluene;

Reference yield:

: 104530-15-6
methyl 3,4-O-isopropylidene-6-O-(1-methoxy-1-methylethyl)-β-D-galactopyranoside

: 151183-18-5
methyl 4-azido-3-O-benzyl-6-O-t-butyldiphenylsilyl-2,4-dideoxy-β-D-arabino-hexoside

Guidance literature:: Multi-step reaction with 11 steps

1: 1.) NaH / 1.) DMF, 0.5 h, 2.) DMF, -10 deg C, 1 h

2: dimethylformamide / 1 h / -10 °C

3: camphor-10-sulfonic acid / methanol; H₂O / 0.5 h

4: 92 percent / tributylstannane / toluene / 14 h / Heating

5: 82 percent / 50percent aq. AcOH / 8 h

6: 76 percent / camphor-10-sulfonic acid / CHCl₃ / 2 h / Heating

7: 93 percent / NaH / dimethylformamide / 2 h

8: 98 percent / 50percent aq. AcOH / CH₂Cl₂ / 6 h

9: ethyldiisopropylamine / dimethylformamide

10: 81 percent / pyridine / CH₂Cl₂ / 3 h

11: 88 percent / NaN₃ / dimethylformamide / 130 °C

With pyridine; sodium azide; camphor-10-sulfonic acid; tri-n-butyl-tin hydride; sodium hydride; acetic acid; N-ethyl-N,N-diisopropylamine; In methanol; dichloromethane; chloroform; water; N,N-dimethyl-formamide; toluene;