(tert-butyl)dimethylsilyl 7-O-acetyl-4,8,10,12,13,14-hexadeoxy-2,3-O-bis-(methoxymethyl)-4,10-dimethyl-15-O-(p-methoxybenzyl)-6-O-[(tert-butyl)dimethylsilyl]-β-D-galacto/β-D-gulo-L-gluco-pentadecopyranosid-9-ulose

Base Information

Chemical Name:(tert-butyl)dimethylsilyl 7-O-acetyl-4,8,10,12,13,14-hexadeoxy-2,3-O-bis-(methoxymethyl)-4,10-dimethyl-15-O-(p-methoxybenzyl)-6-O-[(tert-butyl)dimethylsilyl]-β-D-galacto/β-D-gulo-L-gluco-pentadecopyranosid-9-ulose
CAS No.:278181-39-8
Molecular Formula:C₄₃H₇₈O₁₃Si₂
Molecular Weight:859.256
Hs Code.:

(tert-butyl)dimethylsilyl 7-O-acetyl-4,8,10,12,13,14-hexadeoxy-2,3-O-bis-(methoxymethyl)-4,10-dimethyl-15-O-(p-methoxybenzyl)-6-O-[(tert-butyl)dimethylsilyl]-β-D-galacto/β-D-gulo-L-gluco-pentadecopyranosid-9-ulose

Synonyms:(tert-butyl)dimethylsilyl 7-O-acetyl-4,8,10,12,13,14-hexadeoxy-2,3-O-bis-(methoxymethyl)-4,10-dimethyl-15-O-(p-methoxybenzyl)-6-O-[(tert-butyl)dimethylsilyl]-β-D-galacto/β-D-gulo-L-gluco-pentadecopyranosid-9-ulose

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Chemical Property of (tert-butyl)dimethylsilyl 7-O-acetyl-4,8,10,12,13,14-hexadeoxy-2,3-O-bis-(methoxymethyl)-4,10-dimethyl-15-O-(p-methoxybenzyl)-6-O-[(tert-butyl)dimethylsilyl]-β-D-galacto/β-D-gulo-L-gluco-pentadecopyranosid-9-ulose

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Technology Process of (tert-butyl)dimethylsilyl 7-O-acetyl-4,8,10,12,13,14-hexadeoxy-2,3-O-bis-(methoxymethyl)-4,10-dimethyl-15-O-(p-methoxybenzyl)-6-O-[(tert-butyl)dimethylsilyl]-β-D-galacto/β-D-gulo-L-gluco-pentadecopyranosid-9-ulose

There total 17 articles about (tert-butyl)dimethylsilyl 7-O-acetyl-4,8,10,12,13,14-hexadeoxy-2,3-O-bis-(methoxymethyl)-4,10-dimethyl-15-O-(p-methoxybenzyl)-6-O-[(tert-butyl)dimethylsilyl]-β-D-galacto/β-D-gulo-L-gluco-pentadecopyranosid-9-ulose 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: 100.0%

: 278181-25-2
Acetic acid (4S,5R)-1-{(R)-(tert-butyl-dimethyl-silanyloxy)-[(2R,3R,4R,5S,6R)-6-(tert-butyl-dimethyl-silanyloxy)-4,5-bis-methoxymethoxy-3-methyl-tetrahydro-pyran-2-yl]-methyl}-9-(4-methoxy-benzyloxy)-4-methyl-3-oxo-5-triethylsilanyloxy-nonyl ester

: 278181-39-8
(tert-butyl)dimethylsilyl 7-O-acetyl-4,8,10,12,13,14-hexadeoxy-2,3-O-bis-(methoxymethyl)-4,10-dimethyl-15-O-(p-methoxybenzyl)-6-O-[(tert-butyl)dimethylsilyl]-β-D-galacto/β-D-gulo-L-gluco-pentadecopyranosid-9-ulose

Guidance literature:: With pyridine hydrogenfluoride; In tetrahydrofuran; at -20 - 0 ℃; for 1.25h;
DOI:10.1021/jo991642b

Reference yield:

: 69739-34-0
t-butyldimethylsiyl triflate

: 278181-39-8
(tert-butyl)dimethylsilyl 7-O-acetyl-4,8,10,12,13,14-hexadeoxy-2,3-O-bis-(methoxymethyl)-4,10-dimethyl-15-O-(p-methoxybenzyl)-6-O-[(tert-butyl)dimethylsilyl]-β-D-galacto/β-D-gulo-L-gluco-pentadecopyranosid-9-ulose

Guidance literature:: Multi-step reaction with 6 steps

1.1: 2,6-lutidine / CH₂Cl₂ / 2 h / 0 °C

2.1: DIBAL-H / CH₂Cl₂ / 0.5 h / -78 °C

3.1: 1.74 g / Dess-Martin periodinane / CH₂Cl₂ / 1.5 h / 20 °C

4.1: (i-Pr)2NLi / tetrahydrofuran; hexane / 0.25 h / -78 °C

4.2: tetrahydrofuran; hexane / 0.25 h / -78 °C

5.1: 1.05 g / DMAP; pyridine / 0.67 h / 0 °C

6.1: 100 percent / HF-pyridine / tetrahydrofuran / 1.25 h / -20 - 0 °C

With pyridine; 2,6-dimethylpyridine; dmap; diisobutylaluminium hydride; Dess-Martin periodane; pyridine hydrogenfluoride; lithium diisopropyl amide; In tetrahydrofuran; hexane; dichloromethane; 1.1: Substitution / 2.1: Reduction / 3.1: Oxidation / 4.1: Metallation / 4.2: Addition / 5.1: Acetylation / 6.1: desilylation;
DOI:10.1021/jo991642b

Reference yield:

: 111-29-5
1 ,5-pentanediol

: 278181-39-8
(tert-butyl)dimethylsilyl 7-O-acetyl-4,8,10,12,13,14-hexadeoxy-2,3-O-bis-(methoxymethyl)-4,10-dimethyl-15-O-(p-methoxybenzyl)-6-O-[(tert-butyl)dimethylsilyl]-β-D-galacto/β-D-gulo-L-gluco-pentadecopyranosid-9-ulose

Guidance literature:: Multi-step reaction with 9 steps

1.1: 58 percent / NaH; Bu₄NI / tetrahydrofuran / 0 - 45 °C

2.1: 82 percent / PCC / CH₂Cl₂ / 3 h / 20 °C

3.1: Bu₂BOTf; Et₃N / CH₂Cl₂ / 0.75 h / 0 °C

3.2: 68 percent / CH₂Cl₂ / 3 h / -78 - 0 °C

4.1: AlMe₃ / tetrahydrofuran; heptane / 0.42 h / 0 °C

5.1: 636 mg / imidazole / dimethylformamide / 3 h / 0 - 20 °C

6.1: 90 percent / tetrahydrofuran / 3 h / 0 °C

7.1: (i-Pr)2NLi / tetrahydrofuran; hexane / 0.25 h / -78 °C

7.2: tetrahydrofuran; hexane / 0.25 h / -78 °C

8.1: 1.05 g / DMAP; pyridine / 0.67 h / 0 °C

9.1: 100 percent / HF-pyridine / tetrahydrofuran / 1.25 h / -20 - 0 °C

With pyridine; 1H-imidazole; dmap; di-n-butylboryl trifluoromethanesulfonate; trimethylaluminum; tetra-(n-butyl)ammonium iodide; sodium hydride; pyridine hydrogenfluoride; triethylamine; pyridinium chlorochromate; lithium diisopropyl amide; In tetrahydrofuran; hexane; n-heptane; dichloromethane; N,N-dimethyl-formamide; 1.1: Alkylation / 2.1: Oxidation / 3.1: Metallation / 3.2: Addition / 4.1: Substitution / 5.1: Substitution / 6.1: Substitution / 7.1: Metallation / 7.2: Addition / 8.1: Acetylation / 9.1: desilylation;
DOI:10.1021/jo991642b