6-O-(tert-butyldiphenylsilyl)-2-deoxy-4-O-(diallylphosphono)-3-O-[(R)-3-(tetradecanoyloxy)tetradecanoyl]-2-[(2,2,2-trichloroethoxycarbonyl)amino]-α-D-glucopyranosyl trichloroacetimidate

Base Information

Chemical Name:6-O-(tert-butyldiphenylsilyl)-2-deoxy-4-O-(diallylphosphono)-3-O-[(R)-3-(tetradecanoyloxy)tetradecanoyl]-2-[(2,2,2-trichloroethoxycarbonyl)amino]-α-D-glucopyranosyl trichloroacetimidate
CAS No.:342636-77-5
Molecular Formula:C₆₁H₉₃Cl₆N₂O₁₃PSi
Molecular Weight:1334.19
Hs Code.:

6-O-(tert-butyldiphenylsilyl)-2-deoxy-4-O-(diallylphosphono)-3-O-[(R)-3-(tetradecanoyloxy)tetradecanoyl]-2-[(2,2,2-trichloroethoxycarbonyl)amino]-α-D-glucopyranosyl trichloroacetimidate

Synonyms:6-O-(tert-butyldiphenylsilyl)-2-deoxy-4-O-(diallylphosphono)-3-O-[(R)-3-(tetradecanoyloxy)tetradecanoyl]-2-[(2,2,2-trichloroethoxycarbonyl)amino]-α-D-glucopyranosyl trichloroacetimidate

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Chemical Property of 6-O-(tert-butyldiphenylsilyl)-2-deoxy-4-O-(diallylphosphono)-3-O-[(R)-3-(tetradecanoyloxy)tetradecanoyl]-2-[(2,2,2-trichloroethoxycarbonyl)amino]-α-D-glucopyranosyl trichloroacetimidate

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Technology Process of 6-O-(tert-butyldiphenylsilyl)-2-deoxy-4-O-(diallylphosphono)-3-O-[(R)-3-(tetradecanoyloxy)tetradecanoyl]-2-[(2,2,2-trichloroethoxycarbonyl)amino]-α-D-glucopyranosyl trichloroacetimidate

There total 6 articles about 6-O-(tert-butyldiphenylsilyl)-2-deoxy-4-O-(diallylphosphono)-3-O-[(R)-3-(tetradecanoyloxy)tetradecanoyl]-2-[(2,2,2-trichloroethoxycarbonyl)amino]-α-D-glucopyranosyl trichloroacetimidate 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: 95.0%

: 545-06-2
trichloroacetonitrile

: 6-O-(tert-butyldiphenylsilyl)-2-deoxy-4-O-(diallylphosphono)-3-O-[(R)-3-(tetradecanoyloxy)tetradecanoyl]-2-[(2,2,2-trichloroethoxycarbonyl)amino]-α-D-glucopyranose

: 342636-77-5
6-O-(tert-butyldiphenylsilyl)-2-deoxy-4-O-(diallylphosphono)-3-O-[(R)-3-(tetradecanoyloxy)tetradecanoyl]-2-[(2,2,2-trichloroethoxycarbonyl)amino]-α-D-glucopyranosyl trichloroacetimidate

Guidance literature:: With 1,8-diazabicyclo[5.4.0]undec-7-ene; In dichloromethane; at 20 ℃; for 2h;
DOI:10.1016/S0008-6215(02)00179-9

Reference yield:

: 126429-21-8
diallyl diisopropylphosphoramidite

: 342636-77-5
6-O-(tert-butyldiphenylsilyl)-2-deoxy-4-O-(diallylphosphono)-3-O-[(R)-3-(tetradecanoyloxy)tetradecanoyl]-2-[(2,2,2-trichloroethoxycarbonyl)amino]-α-D-glucopyranosyl trichloroacetimidate

Guidance literature:: Multi-step reaction with 2 steps

1.1: 1H-tetrazole; 30 percent aq. H₂O₂ / tetrahydrofuran / 0 - 20 °C

1.2: 59 percent / I₂ / tetrahydrofuran; H₂O / 2 h / 20 °C

2.1: 95 percent / DBU / CH₂Cl₂ / 2 h / 20 °C

With 1H-tetrazole; dihydrogen peroxide; 1,8-diazabicyclo[5.4.0]undec-7-ene; In tetrahydrofuran; dichloromethane;
DOI:10.1016/S0008-6215(02)00179-9

Reference yield:

: 214050-99-4
(R)-3-Tetradecanoyloxy-tetradecanoic acid (4aR,6S,7R,8R,8aS)-6-allyloxy-2,2-dimethyl-7-(2,2,2-trichloro-ethoxycarbonylamino)-hexahydro-pyrano[3,2-d][1,3]dioxin-8-yl ester

: 342636-77-5
6-O-(tert-butyldiphenylsilyl)-2-deoxy-4-O-(diallylphosphono)-3-O-[(R)-3-(tetradecanoyloxy)tetradecanoyl]-2-[(2,2,2-trichloroethoxycarbonyl)amino]-α-D-glucopyranosyl trichloroacetimidate

Guidance literature:: Multi-step reaction with 4 steps

1.1: p-TsOH / methanol; tetrahydrofuran / 7 h / 20 °C

1.2: 88 percent / imidazole / dimethylformamide / 17 h / 20 °C

2.1: 89 percent / [Ir(C₈H₁₂)(PMePh₂)2]PF₆ / tetrahydrofuran / 1.5 h / 40 °C

3.1: 1H-tetrazole; 30 percent aq. H₂O₂ / tetrahydrofuran / 0 - 20 °C

3.2: 59 percent / I₂ / tetrahydrofuran; H₂O / 2 h / 20 °C

4.1: 95 percent / DBU / CH₂Cl₂ / 2 h / 20 °C

With 1H-tetrazole; (1,5-cyclooctadiene)[bis(methyldiphenylphosphine)]iridium(I) hexafluorophosphate; dihydrogen peroxide; toluene-4-sulfonic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; In tetrahydrofuran; methanol; dichloromethane;
DOI:10.1016/S0008-6215(02)00179-9