allyl 6-O-(tert-butyldiphenylsilyl)-2-deoxy-3-O-[(R)-3-(tetradecanoyloxy)tetradecanoyl]-2-[(2,2,2-trichloroethoxycarbonyl)amino]-α-D-glucopyranoside

Base Information

Chemical Name:allyl 6-O-(tert-butyldiphenylsilyl)-2-deoxy-3-O-[(R)-3-(tetradecanoyloxy)tetradecanoyl]-2-[(2,2,2-trichloroethoxycarbonyl)amino]-α-D-glucopyranoside
CAS No.:342636-75-3
Molecular Formula:C₅₆H₈₈Cl₃NO₁₀Si
Molecular Weight:1069.76
Hs Code.:

allyl 6-O-(tert-butyldiphenylsilyl)-2-deoxy-3-O-[(R)-3-(tetradecanoyloxy)tetradecanoyl]-2-[(2,2,2-trichloroethoxycarbonyl)amino]-α-D-glucopyranoside

Synonyms:allyl 6-O-(tert-butyldiphenylsilyl)-2-deoxy-3-O-[(R)-3-(tetradecanoyloxy)tetradecanoyl]-2-[(2,2,2-trichloroethoxycarbonyl)amino]-α-D-glucopyranoside

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Chemical Property of allyl 6-O-(tert-butyldiphenylsilyl)-2-deoxy-3-O-[(R)-3-(tetradecanoyloxy)tetradecanoyl]-2-[(2,2,2-trichloroethoxycarbonyl)amino]-α-D-glucopyranoside

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Technology Process of allyl 6-O-(tert-butyldiphenylsilyl)-2-deoxy-3-O-[(R)-3-(tetradecanoyloxy)tetradecanoyl]-2-[(2,2,2-trichloroethoxycarbonyl)amino]-α-D-glucopyranoside

There total 1 articles about allyl 6-O-(tert-butyldiphenylsilyl)-2-deoxy-3-O-[(R)-3-(tetradecanoyloxy)tetradecanoyl]-2-[(2,2,2-trichloroethoxycarbonyl)amino]-α-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: 88.0%

: 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

: 58479-61-1
tert-butylchlorodiphenylsilane

: 342636-75-3
allyl 6-O-(tert-butyldiphenylsilyl)-2-deoxy-3-O-[(R)-3-(tetradecanoyloxy)tetradecanoyl]-2-[(2,2,2-trichloroethoxycarbonyl)amino]-α-D-glucopyranoside

Guidance literature:: (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; With toluene-4-sulfonic acid; In tetrahydrofuran; methanol; at 20 ℃; for 7h;

tert-butylchlorodiphenylsilane; With 1H-imidazole; In N,N-dimethyl-formamide; at 20 ℃; for 17h;
DOI:10.1016/S0008-6215(02)00179-9

Reference yield: 89.0%

: 342636-75-3
allyl 6-O-(tert-butyldiphenylsilyl)-2-deoxy-3-O-[(R)-3-(tetradecanoyloxy)tetradecanoyl]-2-[(2,2,2-trichloroethoxycarbonyl)amino]-α-D-glucopyranoside

: 482635-09-6
(E)-1-propenyl 6-O-(tert-butyldiphenylsilyl)-2-deoxy-3-O-[(R)-3-(tetradecanoyloxy)tetradecanoyl]-2-[(2,2,2-trichloroethoxycarbonyl)amino]-α-D-glucopyranoside

Guidance literature:: With (1,5-cyclooctadiene)[bis(methyldiphenylphosphine)]iridium(I) hexafluorophosphate; In tetrahydrofuran; at 40 ℃; for 1.5h;
DOI:10.1016/S0008-6215(02)00179-9

Reference yield:

: 342636-75-3
allyl 6-O-(tert-butyldiphenylsilyl)-2-deoxy-3-O-[(R)-3-(tetradecanoyloxy)tetradecanoyl]-2-[(2,2,2-trichloroethoxycarbonyl)amino]-α-D-glucopyranoside

: 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 3 steps

1.1: 89 percent / [Ir(C₈H₁₂)(PMePh₂)2]PF₆ / tetrahydrofuran / 1.5 h / 40 °C

2.1: 1H-tetrazole; 30 percent aq. H₂O₂ / tetrahydrofuran / 0 - 20 °C

2.2: 59 percent / I₂ / tetrahydrofuran; H₂O / 2 h / 20 °C

3.1: 95 percent / DBU / CH₂Cl₂ / 2 h / 20 °C

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