(3R)-tert-butyl [17-tert-butyldiphenylsilyloxy-3-(2,3,4-tri-O-benzyl-6-O-acetyl-β-D-glucopyranosyl)oxy]heptadecanoate

Base Information

Chemical Name:(3R)-tert-butyl [17-tert-butyldiphenylsilyloxy-3-(2,3,4-tri-O-benzyl-6-O-acetyl-β-D-glucopyranosyl)oxy]heptadecanoate
CAS No.:404867-97-6
Molecular Formula:C₆₆H₉₀O₁₀Si
Molecular Weight:1071.52
Hs Code.:

Synonyms:(3R)-tert-butyl [17-tert-butyldiphenylsilyloxy-3-(2,3,4-tri-O-benzyl-6-O-acetyl-β-D-glucopyranosyl)oxy]heptadecanoate

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Chemical Property of (3R)-tert-butyl [17-tert-butyldiphenylsilyloxy-3-(2,3,4-tri-O-benzyl-6-O-acetyl-β-D-glucopyranosyl)oxy]heptadecanoate

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Technology Process of (3R)-tert-butyl [17-tert-butyldiphenylsilyloxy-3-(2,3,4-tri-O-benzyl-6-O-acetyl-β-D-glucopyranosyl)oxy]heptadecanoate

There total 9 articles about (3R)-tert-butyl [17-tert-butyldiphenylsilyloxy-3-(2,3,4-tri-O-benzyl-6-O-acetyl-β-D-glucopyranosyl)oxy]heptadecanoate 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: 74.0%

: 125164-10-5
6-O-acetyl-2,3,4-tri-O-benzyl-α-D-glucopyranosyl trichloroacetimidate

: 404867-96-5
17-(tert-butyl-diphenyl-silanyloxy)-3-hydroxy-heptadecanoic acid tert-butyl ester

: 404867-97-6
(3R)-tert-butyl [17-tert-butyldiphenylsilyloxy-3-(2,3,4-tri-O-benzyl-6-O-acetyl-β-D-glucopyranosyl)oxy]heptadecanoate

: (3R)-tert-butyl [17-tert-butyldiphenylsilyloxy-3-(2,3,4-tri-O-benzyl-6-O-acetyl-α-D-glucopyranosyl)oxy]heptadecanoate

Guidance literature:: With trimethylsilyl trifluoromethanesulfonate; In dichloromethane; acetonitrile; at -50 ℃; for 0.5h;
DOI:10.1002/chem.200305588

Reference yield:

: 106-02-5,81031-90-5
pentadecanolide

: 404867-97-6
(3R)-tert-butyl [17-tert-butyldiphenylsilyloxy-3-(2,3,4-tri-O-benzyl-6-O-acetyl-β-D-glucopyranosyl)oxy]heptadecanoate

Guidance literature:: Multi-step reaction with 3 steps

1.1: LDA / hexane; tetrahydrofuran / 1 h / -78 °C

1.2: hexane; tetrahydrofuran / 2 h / -40 °C

1.3: 3.1 g / H₂; [RuCl₂(COD)]n; Et₃N / (R)-BINAP / methanol; tetrahydrofuran / 15 h / 70 °C / 11400 Torr

2.1: 81 percent / imidazole / dimethylformamide / 4 h / 20 °C

3.1: 62 percent / 4A molecular sieves; BF₃*Et₂O / CH₂Cl₂ / 2 h / -40 °C

With 1H-imidazole; 4 A molecular sieve; boron trifluoride diethyl etherate; lithium diisopropyl amide; In tetrahydrofuran; hexane; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1021/ja036521e

Reference yield:

: 540-88-5
acetic acid tert-butyl ester

: 404867-97-6
(3R)-tert-butyl [17-tert-butyldiphenylsilyloxy-3-(2,3,4-tri-O-benzyl-6-O-acetyl-β-D-glucopyranosyl)oxy]heptadecanoate

Guidance literature:: Multi-step reaction with 4 steps

1.1: LDA / tetrahydrofuran; hexane / 1 h / -78 °C

1.2: tetrahydrofuran; hexane / 2 h / -40 °C

2.1: 88 percent / H₂ / [(R)-BINAP*RuCl₂]2*NEt₃ / methanol; tetrahydrofuran / 15 h / 70 °C / 11400.8 Torr

3.1: 81 percent / imidazole / dimethylformamide / 4 h / 20 °C

4.1: molecular sieves 4 Angstroem; BF₃*Et₂O / CH₂Cl₂ / 2 h / -40 °C

With 1H-imidazole; 4 A molecular sieve; boron trifluoride diethyl etherate; hydrogen; lithium diisopropyl amide; [(R)-BINAP RuCl₂]2NEt₃; In tetrahydrofuran; methanol; hexane; dichloromethane; N,N-dimethyl-formamide; 1.2: ring-opening Claisen condensation;
DOI:10.1021/ja0175791