methyl 2-O-acetyl-3-O-benzyl-4-O-tert-butyldimethylsilyl-α-L-idopyranosyluronate-(1→4)-tert-butyldimethylsilyl (2-azido-3-O-benzyl-6-O-levulinoyl-2-deoxy-β-D-glucopyranoside)

Base Information

Chemical Name:methyl 2-O-acetyl-3-O-benzyl-4-O-tert-butyldimethylsilyl-α-L-idopyranosyluronate-(1→4)-tert-butyldimethylsilyl (2-azido-3-O-benzyl-6-O-levulinoyl-2-deoxy-β-D-glucopyranoside)
CAS No.:1448263-57-7
Molecular Formula:C₄₆H₆₉N₃O₁₄Si₂
Molecular Weight:944.237
Hs Code.:

methyl 2-O-acetyl-3-O-benzyl-4-O-tert-butyldimethylsilyl-α-L-idopyranosyluronate-(1→4)-tert-butyldimethylsilyl (2-azido-3-O-benzyl-6-O-levulinoyl-2-deoxy-β-D-glucopyranoside)

Synonyms:methyl 2-O-acetyl-3-O-benzyl-4-O-tert-butyldimethylsilyl-α-L-idopyranosyluronate-(1→4)-tert-butyldimethylsilyl (2-azido-3-O-benzyl-6-O-levulinoyl-2-deoxy-β-D-glucopyranoside)

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Chemical Property of methyl 2-O-acetyl-3-O-benzyl-4-O-tert-butyldimethylsilyl-α-L-idopyranosyluronate-(1→4)-tert-butyldimethylsilyl (2-azido-3-O-benzyl-6-O-levulinoyl-2-deoxy-β-D-glucopyranoside)

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Technology Process of methyl 2-O-acetyl-3-O-benzyl-4-O-tert-butyldimethylsilyl-α-L-idopyranosyluronate-(1→4)-tert-butyldimethylsilyl (2-azido-3-O-benzyl-6-O-levulinoyl-2-deoxy-β-D-glucopyranoside)

There total 6 articles about methyl 2-O-acetyl-3-O-benzyl-4-O-tert-butyldimethylsilyl-α-L-idopyranosyluronate-(1→4)-tert-butyldimethylsilyl (2-azido-3-O-benzyl-6-O-levulinoyl-2-deoxy-β-D-glucopyranoside) 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: 93.0%

: methyl (dibutylphosphate-2-O-acetyl-3-O-benzyl-4-O-tert-butyldimethylsilyl-α-L-idopyranosid)uronate

: C₂₄H₃₇N₃O₇Si

: 1448263-57-7
methyl 2-O-acetyl-3-O-benzyl-4-O-tert-butyldimethylsilyl-α-L-idopyranosyluronate-(1→4)-tert-butyldimethylsilyl (2-azido-3-O-benzyl-6-O-levulinoyl-2-deoxy-β-D-glucopyranoside)

Guidance literature:: methyl (dibutylphosphate-2-O-acetyl-3-O-benzyl-4-O-tert-butyldimethylsilyl-α-L-idopyranosid)uronate; C₂₄H₃₇N₃O₇Si; In dichloromethane; toluene; at -10 - 20 ℃; for 0.5h; Molecular sieve;

With trimethylsilyl trifluoromethanesulfonate; In dichloromethane; toluene; at -30 ℃; for 0.5h;

Reference yield: 93.0%

: methyl (dibutylphosphate-2-O-acetyl-3-O-benzyl-4-O-tert-butyldimethylsilyl-β-L-idopyranosid)uronate

: 1448263-54-4
2-O-azido-3-O-benzyl-6-O-levulinoyl-1-O-tert-butyldimethylsilyl-2-deoxy-β-D-glucopyranoside

: 1448263-57-7
methyl 2-O-acetyl-3-O-benzyl-4-O-tert-butyldimethylsilyl-α-L-idopyranosyluronate-(1→4)-tert-butyldimethylsilyl (2-azido-3-O-benzyl-6-O-levulinoyl-2-deoxy-β-D-glucopyranoside)

Guidance literature:: methyl (dibutylphosphate-2-O-acetyl-3-O-benzyl-4-O-tert-butyldimethylsilyl-β-L-idopyranosid)uronate; 2-O-azido-3-O-benzyl-6-O-levulinoyl-1-O-tert-butyldimethylsilyl-2-deoxy-β-D-glucopyranoside; In dichloromethane; at -10 - 20 ℃; for 0.5h; Inert atmosphere; Molecular sieve;

With trimethylsilyl trifluoromethanesulfonate; In dichloromethane; at -30 ℃; for 0.5h; Inert atmosphere; Molecular sieve;
DOI:10.1021/ja4027727

Reference yield:

: 87326-79-2
methyl 1,2,4-tri-O-acetyl-3-O-benzyl-β-L-idopyranosyluronate

: 1448263-57-7
methyl 2-O-acetyl-3-O-benzyl-4-O-tert-butyldimethylsilyl-α-L-idopyranosyluronate-(1→4)-tert-butyldimethylsilyl (2-azido-3-O-benzyl-6-O-levulinoyl-2-deoxy-β-D-glucopyranoside)

Guidance literature:: Multi-step reaction with 5 steps

1.1: titanium(IV) bromide / dichloromethane / 16 h / 20 °C / Darkness; Inert atmosphere

1.2: 14 h / 20 °C / Inert atmosphere

2.1: sodium methylate / methanol / -10 - 5 °C / Inert atmosphere

3.1: pyridine / -10 - 0 °C / Inert atmosphere

4.1: dichloromethane / 0.25 h / 20 °C / Inert atmosphere; Molecular sieve

4.2: Inert atmosphere; Molecular sieve

5.1: dichloromethane / 0.5 h / -10 - 20 °C / Inert atmosphere; Molecular sieve

5.2: 0.5 h / -30 °C / Inert atmosphere; Molecular sieve

With pyridine; sodium methylate; titanium(IV) bromide; In methanol; dichloromethane;
DOI:10.1021/ja4027727