t-butyldimethylsilyl 2,3,7,8-tetradeoxy-4-O-(4-methoxybenzyl)-3,5-di-C-methyl-α-L-xylo-octopyranosid-6-ulose

Base Information

Chemical Name:t-butyldimethylsilyl 2,3,7,8-tetradeoxy-4-O-(4-methoxybenzyl)-3,5-di-C-methyl-α-L-xylo-octopyranosid-6-ulose
CAS No.:158648-97-6
Molecular Formula:C₂₄H₄₀O₅Si
Molecular Weight:436.664
Hs Code.:

Synonyms:t-butyldimethylsilyl 2,3,7,8-tetradeoxy-4-O-(4-methoxybenzyl)-3,5-di-C-methyl-α-L-xylo-octopyranosid-6-ulose

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Chemical Property of t-butyldimethylsilyl 2,3,7,8-tetradeoxy-4-O-(4-methoxybenzyl)-3,5-di-C-methyl-α-L-xylo-octopyranosid-6-ulose

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Technology Process of t-butyldimethylsilyl 2,3,7,8-tetradeoxy-4-O-(4-methoxybenzyl)-3,5-di-C-methyl-α-L-xylo-octopyranosid-6-ulose

There total 11 articles about t-butyldimethylsilyl 2,3,7,8-tetradeoxy-4-O-(4-methoxybenzyl)-3,5-di-C-methyl-α-L-xylo-octopyranosid-6-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: 48.5%

: 18162-48-6
tert-butyldimethylsilyl chloride

: 163228-86-2
(3R,4S,5R)-5-Hydroxy-4-(4-methoxy-benzyloxy)-3,5-dimethyl-6-oxo-octanal

: t-butyldimethylsilyl 2,3,7,8-tetradeoxy-4-O-(4-methoxybenzyl)-3,5-di-C-methyl-β-L-xylo-octopyranosid-6-ulose

: 158648-97-6
t-butyldimethylsilyl 2,3,7,8-tetradeoxy-4-O-(4-methoxybenzyl)-3,5-di-C-methyl-α-L-xylo-octopyranosid-6-ulose

Guidance literature:: With 1H-imidazole; In N,N-dimethyl-formamide; at 40 ℃; for 12h;
DOI:10.1246/bcsj.68.967

Reference yield:

: 158586-21-1
(2R,3S,4R)-4-methyl-2-(triethylsilyloxy)-5-hexen-3-ol

: 158648-97-6
t-butyldimethylsilyl 2,3,7,8-tetradeoxy-4-O-(4-methoxybenzyl)-3,5-di-C-methyl-α-L-xylo-octopyranosid-6-ulose

Guidance literature:: Multi-step reaction with 11 steps

1: 55 percent / CSA / hexane / 72 h / 25 °C

2: 1.) BH₃*SMe₂, cyclohexene, 2.) aq. NaOH, H₂O₂ / 1.) THF, 0 deg C, 1 h, 2.) 51 deg C, 20 min

3: Dess-Martin periodinane, pyridine / CH₂Cl₂ / 1 h / 25 °C

4: benzene / 12 h / 45 °C

5: 100 percent / n-Bu₄NF / tetrahydrofuran / 1.5 h / 25 °C

6: 95 percent / Dess-Martin periodinane, pyridine / CH₂Cl₂ / 0.5 h / 25 °C

7: 70 percent / benzene; diethyl ether / 2 h / -78 °C

8: 92 percent / L-selectride / tetrahydrofuran / 1 h / -100 °C

9: OsO₄, NMO, water / acetone / 12 h / 25 °C

10: NaIO₄ / H₂O; tetrahydrofuran / 1 h / 25 °C

11: 48.5 percent / imidazole / dimethylformamide / 12 h / 40 °C

With pyridine; 1H-imidazole; sodium hydroxide; sodium periodate; osmium(VIII) oxide; N-methyl-2-indolinone; dimethylsulfide borane complex; camphor-10-sulfonic acid; tetrabutyl ammonium fluoride; water; dihydrogen peroxide; L-Selectride; Dess-Martin periodane; cyclohexene; In tetrahydrofuran; diethyl ether; hexane; dichloromethane; water; N,N-dimethyl-formamide; acetone; benzene;
DOI:10.1246/bcsj.68.967

Reference yield:

: 163228-84-0
(2R,3S,4R)-3-(4-Methoxy-benzyloxy)-4-methyl-hept-6-en-2-ol

: 158648-97-6
t-butyldimethylsilyl 2,3,7,8-tetradeoxy-4-O-(4-methoxybenzyl)-3,5-di-C-methyl-α-L-xylo-octopyranosid-6-ulose

Guidance literature:: Multi-step reaction with 6 steps

1: 95 percent / Dess-Martin periodinane, pyridine / CH₂Cl₂ / 0.5 h / 25 °C

2: 70 percent / benzene; diethyl ether / 2 h / -78 °C

3: 92 percent / L-selectride / tetrahydrofuran / 1 h / -100 °C

4: OsO₄, NMO, water / acetone / 12 h / 25 °C

5: NaIO₄ / H₂O; tetrahydrofuran / 1 h / 25 °C

6: 48.5 percent / imidazole / dimethylformamide / 12 h / 40 °C

With pyridine; 1H-imidazole; sodium periodate; osmium(VIII) oxide; N-methyl-2-indolinone; water; L-Selectride; Dess-Martin periodane; In tetrahydrofuran; diethyl ether; dichloromethane; water; N,N-dimethyl-formamide; acetone; benzene;
DOI:10.1246/bcsj.68.967