(25R)-15α-(2-acetylamino-3,4,6-tri-O-benzyl-2-deoxy-β-D-glucopyranosyloxy)-3α-hydroxy-5α-cholestan-26-yl acetate

Base Information

Chemical Name:(25R)-15α-(2-acetylamino-3,4,6-tri-O-benzyl-2-deoxy-β-D-glucopyranosyloxy)-3α-hydroxy-5α-cholestan-26-yl acetate
CAS No.:872465-39-9
Molecular Formula:C₅₈H₈₁NO₉
Molecular Weight:936.282
Hs Code.:

Synonyms:(25R)-15α-(2-acetylamino-3,4,6-tri-O-benzyl-2-deoxy-β-D-glucopyranosyloxy)-3α-hydroxy-5α-cholestan-26-yl acetate

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Chemical Property of (25R)-15α-(2-acetylamino-3,4,6-tri-O-benzyl-2-deoxy-β-D-glucopyranosyloxy)-3α-hydroxy-5α-cholestan-26-yl acetate

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Technology Process of (25R)-15α-(2-acetylamino-3,4,6-tri-O-benzyl-2-deoxy-β-D-glucopyranosyloxy)-3α-hydroxy-5α-cholestan-26-yl acetate

There total 11 articles about (25R)-15α-(2-acetylamino-3,4,6-tri-O-benzyl-2-deoxy-β-D-glucopyranosyloxy)-3α-hydroxy-5α-cholestan-26-yl acetate 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: 80.0%

: 872465-38-8
(25R)-3α,26-dihydroxy-5α-cholestan-15α-yl 2-(acetylamino)-3,4,6-tri-O-benzyl-2-deoxy-β-D-glucopyranoside

: 108-05-4,9003-20-7
vinyl acetate

: 872465-39-9
(25R)-15α-(2-acetylamino-3,4,6-tri-O-benzyl-2-deoxy-β-D-glucopyranosyloxy)-3α-hydroxy-5α-cholestan-26-yl acetate

Guidance literature:: With Bu₈Sn₄Cl₄O₂; In dichloromethane; at 20 ℃; for 12h;
DOI:10.1021/jo051733a

Reference yield:

: 872465-33-3
(25R)-5α-cholest-16-ene-3α,26-diol 3,26-dibenzoate

: 872465-39-9
(25R)-15α-(2-acetylamino-3,4,6-tri-O-benzyl-2-deoxy-β-D-glucopyranosyloxy)-3α-hydroxy-5α-cholestan-26-yl acetate

Guidance literature:: Multi-step reaction with 6 steps

1: 60 percent / chromium trioxide; 3,5-dimethylpyrazole / CH₂Cl₂ / 5 h / -20 °C

2: 98 percent / NaBH₄; cerium trichloride / tetrahydrofuran; methanol / 2 h / 20 °C

3: 98 percent / H₂ / Pd(OH)2/C / ethyl acetate / 3 h

4: 72 percent / AgClO₄; SnCl₂ / CH₂Cl₂ / 16 h / 0 °C

5: 90 percent / KOH / methanol; CH₂Cl₂ / 12 h / Heating

6: 80 percent / Bu₈Sn₄Cl₄O₂ / CH₂Cl₂ / 12 h / 20 °C

With 3,5-dimethyl-1H-pyrazole; chromium(VI) oxide; potassium hydroxide; sodium tetrahydroborate; cerium(III) chloride; Bu₈Sn₄Cl₄O₂; hydrogen; silver perchlorate; tin(ll) chloride; palladium dihydroxide; In tetrahydrofuran; methanol; dichloromethane; ethyl acetate; 2: Luche reduction / 6: Otera's transesterification;
DOI:10.1021/jo051733a

Reference yield:

: 872465-34-4
(25R)-3α,26-dihydroxy-5α-cholest-16-en-15-one 3,26-dibenzoate

: 872465-39-9
(25R)-15α-(2-acetylamino-3,4,6-tri-O-benzyl-2-deoxy-β-D-glucopyranosyloxy)-3α-hydroxy-5α-cholestan-26-yl acetate

Guidance literature:: Multi-step reaction with 5 steps

1: 98 percent / NaBH₄; cerium trichloride / tetrahydrofuran; methanol / 2 h / 20 °C

2: 98 percent / H₂ / Pd(OH)2/C / ethyl acetate / 3 h

3: 72 percent / AgClO₄; SnCl₂ / CH₂Cl₂ / 16 h / 0 °C

4: 90 percent / KOH / methanol; CH₂Cl₂ / 12 h / Heating

5: 80 percent / Bu₈Sn₄Cl₄O₂ / CH₂Cl₂ / 12 h / 20 °C

With potassium hydroxide; sodium tetrahydroborate; cerium(III) chloride; Bu₈Sn₄Cl₄O₂; hydrogen; silver perchlorate; tin(ll) chloride; palladium dihydroxide; In tetrahydrofuran; methanol; dichloromethane; ethyl acetate; 1: Luche reduction / 5: Otera's transesterification;
DOI:10.1021/jo051733a