O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-(1->3)-2-O-acetyl-6-O-tert-butyldiphenylsilyl-4-O-(4-methylbenzoyl)-D-galactopyranosyl trichloroacetimidate

Base Information

Chemical Name:O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-(1->3)-2-O-acetyl-6-O-tert-butyldiphenylsilyl-4-O-(4-methylbenzoyl)-D-galactopyranosyl trichloroacetimidate
CAS No.:343254-46-6
Molecular Formula:C₄₈H₅₆Cl₃NO₁₇Si
Molecular Weight:1053.41
Hs Code.:

O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-(1->3)-2-O-acetyl-6-O-tert-butyldiphenylsilyl-4-O-(4-methylbenzoyl)-D-galactopyranosyl trichloroacetimidate

Synonyms:O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-(1->3)-2-O-acetyl-6-O-tert-butyldiphenylsilyl-4-O-(4-methylbenzoyl)-D-galactopyranosyl trichloroacetimidate

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Chemical Property of O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-(1->3)-2-O-acetyl-6-O-tert-butyldiphenylsilyl-4-O-(4-methylbenzoyl)-D-galactopyranosyl trichloroacetimidate

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Technology Process of O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-(1->3)-2-O-acetyl-6-O-tert-butyldiphenylsilyl-4-O-(4-methylbenzoyl)-D-galactopyranosyl trichloroacetimidate

There total 7 articles about O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-(1->3)-2-O-acetyl-6-O-tert-butyldiphenylsilyl-4-O-(4-methylbenzoyl)-D-galactopyranosyl 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: 93.0%

: 545-06-2
trichloroacetonitrile

: 343254-52-4
4-methoxyphenyl O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-(1->3)-2-O-acetyl-6-O-tert-butyldiphenylsilyl-4-O-(4-methylbenzoyl)-β-D-galactopyranoside

: 343254-46-6
O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-(1->3)-2-O-acetyl-6-O-tert-butyldiphenylsilyl-4-O-(4-methylbenzoyl)-D-galactopyranosyl trichloroacetimidate

Guidance literature:: 4-methoxyphenyl O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-(1->3)-2-O-acetyl-6-O-tert-butyldiphenylsilyl-4-O-(4-methylbenzoyl)-β-D-galactopyranoside; With ammonium cerium(IV) nitrate; In water; acetonitrile; at 0 ℃; for 0.833333h;

trichloroacetonitrile; With 1,8-diazabicyclo[5.4.0]undec-7-ene; In dichloromethane; at 0 - 20 ℃; for 0.833333h; Further stages.;
DOI:10.1021/jo001540h

Reference yield:

: 144985-19-3
p-methoxyphenyl 3-O-allyl-β-D-galactopyranoside

: 343254-46-6
O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-(1->3)-2-O-acetyl-6-O-tert-butyldiphenylsilyl-4-O-(4-methylbenzoyl)-D-galactopyranosyl trichloroacetimidate

Guidance literature:: Multi-step reaction with 6 steps

1.1: pyridine

2.1: Et₃N / methanol; H₂O / 16 h / 20 °C

2.2: 85 percent / imidazole / dimethylformamide / 20 °C

3.1: 97 percent / DMAP / pyridine

4.1: H₂ / Ir(COD)(PMePh₂)PF₆ / tetrahydrofuran / 2 h

4.2: 99 percent / I₂; NaHCO₃ / H₂O; tetrahydrofuran / 0.25 h

5.1: 43 percent / MS AW₃₀₀; TMSOTf / CH₂Cl₂ / 2 h / -20 °C

6.1: CAN / acetonitrile; H₂O / 0.83 h / 0 °C

6.2: 93 percent / DBU / CH₂Cl₂ / 0.83 h / 0 - 20 °C

With dmap; ammonium cerium(IV) nitrate; trimethylsilyl trifluoromethanesulfonate; MS AW₃₀₀; hydrogen; triethylamine; (1,5-cyclooctadiene)[bis(methyldiphenylphosphine)]iridium(I) hexafluorophosphate; In tetrahydrofuran; pyridine; methanol; dichloromethane; water; acetonitrile;
DOI:10.1021/jo001540h

Reference yield:

: 58479-61-1
tert-butylchlorodiphenylsilane

: 343254-46-6
O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-(1->3)-2-O-acetyl-6-O-tert-butyldiphenylsilyl-4-O-(4-methylbenzoyl)-D-galactopyranosyl trichloroacetimidate

Guidance literature:: Multi-step reaction with 5 steps

1.1: Et₃N / methanol; H₂O / 16 h / 20 °C

1.2: 85 percent / imidazole / dimethylformamide / 20 °C

2.1: 97 percent / DMAP / pyridine

3.1: H₂ / Ir(COD)(PMePh₂)PF₆ / tetrahydrofuran / 2 h

3.2: 99 percent / I₂; NaHCO₃ / H₂O; tetrahydrofuran / 0.25 h

4.1: 43 percent / MS AW₃₀₀; TMSOTf / CH₂Cl₂ / 2 h / -20 °C

5.1: CAN / acetonitrile; H₂O / 0.83 h / 0 °C

5.2: 93 percent / DBU / CH₂Cl₂ / 0.83 h / 0 - 20 °C

With dmap; ammonium cerium(IV) nitrate; trimethylsilyl trifluoromethanesulfonate; MS AW₃₀₀; hydrogen; triethylamine; (1,5-cyclooctadiene)[bis(methyldiphenylphosphine)]iridium(I) hexafluorophosphate; In tetrahydrofuran; pyridine; methanol; dichloromethane; water; acetonitrile;
DOI:10.1021/jo001540h