methyl (methyl 4-O-[2-azido-6-O-(tert-butyldiphenylsilyl)-2-deoxy-3-O-levulinoyl-4-O-(p-methoxybenzyl)-α-D-glucopyranosyl]-2-O-acetyl-3-O-[2-(trimethylsilyl)ethoxymethyl]-α-D-glucopyranosyluronate)

Base Information

Chemical Name:methyl (methyl 4-O-[2-azido-6-O-(tert-butyldiphenylsilyl)-2-deoxy-3-O-levulinoyl-4-O-(p-methoxybenzyl)-α-D-glucopyranosyl]-2-O-acetyl-3-O-[2-(trimethylsilyl)ethoxymethyl]-α-D-glucopyranosyluronate)
CAS No.:870001-64-2
Molecular Formula:C₅₁H₇₁N₃O₁₆Si₂
Molecular Weight:1038.31
Hs Code.:

methyl (methyl 4-O-[2-azido-6-O-(tert-butyldiphenylsilyl)-2-deoxy-3-O-levulinoyl-4-O-(p-methoxybenzyl)-α-D-glucopyranosyl]-2-O-acetyl-3-O-[2-(trimethylsilyl)ethoxymethyl]-α-D-glucopyranosyluronate)

Synonyms:methyl (methyl 4-O-[2-azido-6-O-(tert-butyldiphenylsilyl)-2-deoxy-3-O-levulinoyl-4-O-(p-methoxybenzyl)-α-D-glucopyranosyl]-2-O-acetyl-3-O-[2-(trimethylsilyl)ethoxymethyl]-α-D-glucopyranosyluronate)

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Chemical Property of methyl (methyl 4-O-[2-azido-6-O-(tert-butyldiphenylsilyl)-2-deoxy-3-O-levulinoyl-4-O-(p-methoxybenzyl)-α-D-glucopyranosyl]-2-O-acetyl-3-O-[2-(trimethylsilyl)ethoxymethyl]-α-D-glucopyranosyluronate)

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Technology Process of methyl (methyl 4-O-[2-azido-6-O-(tert-butyldiphenylsilyl)-2-deoxy-3-O-levulinoyl-4-O-(p-methoxybenzyl)-α-D-glucopyranosyl]-2-O-acetyl-3-O-[2-(trimethylsilyl)ethoxymethyl]-α-D-glucopyranosyluronate)

There total 16 articles about methyl (methyl 4-O-[2-azido-6-O-(tert-butyldiphenylsilyl)-2-deoxy-3-O-levulinoyl-4-O-(p-methoxybenzyl)-α-D-glucopyranosyl]-2-O-acetyl-3-O-[2-(trimethylsilyl)ethoxymethyl]-α-D-glucopyranosyluronate) 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: 74.0%

: 870001-86-8
(2S,3S,4S,5R,6S)-5-Acetoxy-3-[(2R,3R,4R,5S,6R)-3-azido-6-(tert-butyl-diphenyl-silanyloxymethyl)-5-(4-methoxy-benzyloxy)-4-(4-oxo-pentanoyloxy)-tetrahydro-pyran-2-yloxy]-4-hydroxy-6-methoxy-tetrahydro-pyran-2-carboxylic acid methyl ester

: 76513-69-4
(2-trimethylethylsilylethoxy)methyl chloride

: 870001-64-2
methyl (methyl 4-O-[2-azido-6-O-(tert-butyldiphenylsilyl)-2-deoxy-3-O-levulinoyl-4-O-(p-methoxybenzyl)-α-D-glucopyranosyl]-2-O-acetyl-3-O-[2-(trimethylsilyl)ethoxymethyl]-α-D-glucopyranosyluronate)

Guidance literature:: With tetra-(n-butyl)ammonium iodide; N-ethyl-N,N-diisopropylamine; In dichloromethane; at 20 ℃; for 48h;
DOI:10.1021/ol052130o

Reference yield: 25.0%

: (2S,3S,4S,5R,6S)-5-Acetoxy-3-hydroxy-6-methoxy-4-(2-trimethylsilanyl-ethoxymethoxy)-tetrahydro-pyran-2-carboxylic acid methyl ester

: 870001-62-0
p-tolyl 2-azido-6-O-(tert-butyldiphenylsilyl)-1,2-deoxy-3-levulinoyl-4-O-(p-methoxybenzyl)-1-thio-β-D-glucopyranoside

: 870001-64-2
methyl (methyl 4-O-[2-azido-6-O-(tert-butyldiphenylsilyl)-2-deoxy-3-O-levulinoyl-4-O-(p-methoxybenzyl)-α-D-glucopyranosyl]-2-O-acetyl-3-O-[2-(trimethylsilyl)ethoxymethyl]-α-D-glucopyranosyluronate)

Guidance literature:: p-tolyl 2-azido-6-O-(tert-butyldiphenylsilyl)-1,2-deoxy-3-levulinoyl-4-O-(p-methoxybenzyl)-1-thio-β-D-glucopyranoside; With 1-benzenesulfinyl piperidine; trifluoromethylsulfonic anhydride; 4 A molecular sieve; 2,6-di-tert-butyl-4-methylpyridine; In dichloromethane; at -60 ℃;

(2S,3S,4S,5R,6S)-5-Acetoxy-3-hydroxy-6-methoxy-4-(2-trimethylsilanyl-ethoxymethoxy)-tetrahydro-pyran-2-carboxylic acid methyl ester; In dichloromethane; at -60 - 20 ℃; for 20h;
DOI:10.1021/ol052130o

Reference yield:

: p-tolyl 3-O-acetyl-1,2-deoxy-4,6-O-(p-methoxybenzylidene)-2-phthalimido-1-thio-β-D-glucopyranoside

: 870001-64-2
methyl (methyl 4-O-[2-azido-6-O-(tert-butyldiphenylsilyl)-2-deoxy-3-O-levulinoyl-4-O-(p-methoxybenzyl)-α-D-glucopyranosyl]-2-O-acetyl-3-O-[2-(trimethylsilyl)ethoxymethyl]-α-D-glucopyranosyluronate)

Guidance literature:: Multi-step reaction with 7 steps

1.1: 84 percent / Bu₂BOTf; BH₃*THF / tetrahydrofuran; CH₂Cl₂ / 1.5 h / -20 - -5 °C

2.1: 88 percent / imidazole / dimethylformamide / 24 h / 20 °C

3.1: NaOMe / CH₂Cl₂; methanol / 4 h / 20 °C

4.1: ethylenediamine / butan-1-ol / 12 h / 100 °C

5.1: 0.600 g / CuSO₄*5H₂O; potassium carbonate; TfN₃ / methanol; H₂O / 48 h / 20 °C

6.1: 90 percent / DCC; 4-(dimethylamino)pyridine / CH₂Cl₂ / 0 - 20 °C

7.1: N-benzenesulfinyl piperidine; Tf₂O; molecular sieves 4 Angstroem / DTBMP / CH₂Cl₂ / -60 °C

7.2: 25 percent / CH₂Cl₂ / 20 h / -60 - 20 °C

With 1H-imidazole; dmap; borane-THF; 1-benzenesulfinyl piperidine; trifluoromethylsulfonic anhydride; 4 A molecular sieve; di-n-butylboryl trifluoromethanesulfonate; triflic azide; sodium methylate; potassium carbonate; copper(II) sulfate; ethylenediamine; dicyclohexyl-carbodiimide; 2,6-di-tert-butyl-4-methylpyridine; In tetrahydrofuran; methanol; dichloromethane; water; N,N-dimethyl-formamide; butan-1-ol;
DOI:10.1021/ol052130o