(1R,2S,3S)-6-benzyloxy-3-acetoxy-2-tert-butoxycarbonylamino-1-(6-methoxyquinol-4-yl)-1-triethylsilyloxy-hexane

Base Information

• Chemical Name: (1R,2S,3S)-6-benzyloxy-3-acetoxy-2-tert-butoxycarbonylamino-1-(6-methoxyquinol-4-yl)-1-triethylsilyloxy-hexane
• CAS No.: 911319-67-0
• Molecular Formula: C₃₆H₅₂N₂O₇Si
• Molecular Weight: 652.904

Synonyms:(1R,2S,3S)-6-benzyloxy-3-acetoxy-2-tert-butoxycarbonylamino-1-(6-methoxyquinol-4-yl)-1-triethylsilyloxy-hexane

Chemical Property of (1R,2S,3S)-6-benzyloxy-3-acetoxy-2-tert-butoxycarbonylamino-1-(6-methoxyquinol-4-yl)-1-triethylsilyloxy-hexane

Chemical Property:

Purity/Quality:

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Technology Process of (1R,2S,3S)-6-benzyloxy-3-acetoxy-2-tert-butoxycarbonylamino-1-(6-methoxyquinol-4-yl)-1-triethylsilyloxy-hexane

There total 13 articles about (1R,2S,3S)-6-benzyloxy-3-acetoxy-2-tert-butoxycarbonylamino-1-(6-methoxyquinol-4-yl)-1-triethylsilyloxy-hexane 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: 100.0%

(1R,2S,3S)-6-benzyloxy-2-tert-butoxycarbonylamino-3-hydroxy-1-(6-methoxyquinol-4-yl)-1-triethylsilyloxy-hexane (911319-46-5) + acetic anhydride (108-24-7) → (1R,2S,3S)-6-benzyloxy-3-acetoxy-2-tert-butoxycarbonylamino-1-(6-methoxyquinol-4-yl)-1-triethylsilyloxy-hexane (911319-67-0)

Guidance literature:

With dmap; In dichloromethane; at 20 ℃; for 3h;

DOI:10.1021/ol061524s

Reference yield:

(3R,5R,6S)-3-[(R)-Hydroxy-(6-methoxy-quinolin-4-yl)-methyl]-2-oxo-5,6-diphenyl-morpholine-4-carboxylic acid benzyl ester (911319-42-1) → (1R,2S,3S)-6-benzyloxy-3-acetoxy-2-tert-butoxycarbonylamino-1-(6-methoxyquinol-4-yl)-1-triethylsilyloxy-hexane (911319-67-0)

Guidance literature:

Multi-step reaction with 9 steps

1.1: 99 percent / DMAP / CH₂Cl₂; tetrahydrofuran / 12 h / Heating

2.1: H₂ / Pd/C / ethyl acetate / 12 h / 20 °C / atmospheric pressure

3.1: ZnCl₂ / 24 h / 50 °C

4.1: Pb(OAc)4 / methanol; CH₂Cl₂ / 0.08 h / 0 °C

4.2: 1.28 g / H₂ / Pd/C / ethyl acetate / 24 h / 20 °C / atmospheric pressure

5.1: 81 percent / DIBAL-H / toluene; hexane / -78 °C

6.1: Mg; I₂ / diethyl ether / 1 h / 20 °C

6.2: 87 percent / tetrahydrofuran; diethyl ether / 0.25 h / -78 °C

7.1: 85 percent / Dess-Martin periodinane / CH₂Cl₂ / 1 h / 20 °C

8.1: DIBAL-H / tetrahydrofuran; hexane / -78 - 0 °C

9.1: 100 percent / DMAP / CH₂Cl₂ / 3 h / 20 °C

With lead(IV) acetate; dmap; hydrogen; iodine; diisobutylaluminium hydride; Dess-Martin periodane; magnesium; zinc(II) chloride; palladium on activated charcoal; In tetrahydrofuran; methanol; diethyl ether; hexane; dichloromethane; ethyl acetate; toluene;

DOI:10.1021/ol061524s

Reference yield:

(3R,5R,6S)-3-[(R)-(6-Methoxy-quinolin-4-yl)-triethylsilanyloxy-methyl]-2-oxo-5,6-diphenyl-morpholine-4-carboxylic acid benzyl ester (911319-43-2) → (1R,2S,3S)-6-benzyloxy-3-acetoxy-2-tert-butoxycarbonylamino-1-(6-methoxyquinol-4-yl)-1-triethylsilyloxy-hexane (911319-67-0)

Guidance literature:

Multi-step reaction with 8 steps

1.1: H₂ / Pd/C / ethyl acetate / 12 h / 20 °C / atmospheric pressure

2.1: ZnCl₂ / 24 h / 50 °C

3.1: Pb(OAc)4 / methanol; CH₂Cl₂ / 0.08 h / 0 °C

3.2: 1.28 g / H₂ / Pd/C / ethyl acetate / 24 h / 20 °C / atmospheric pressure

4.1: 81 percent / DIBAL-H / toluene; hexane / -78 °C

5.1: Mg; I₂ / diethyl ether / 1 h / 20 °C

5.2: 87 percent / tetrahydrofuran; diethyl ether / 0.25 h / -78 °C

6.1: 85 percent / Dess-Martin periodinane / CH₂Cl₂ / 1 h / 20 °C

7.1: DIBAL-H / tetrahydrofuran; hexane / -78 - 0 °C

8.1: 100 percent / DMAP / CH₂Cl₂ / 3 h / 20 °C

With lead(IV) acetate; dmap; hydrogen; iodine; diisobutylaluminium hydride; Dess-Martin periodane; magnesium; zinc(II) chloride; palladium on activated charcoal; In tetrahydrofuran; methanol; diethyl ether; hexane; dichloromethane; ethyl acetate; toluene;

DOI:10.1021/ol061524s

upstream raw materials:

(1R,2S,3S)-6-benzyloxy-2-tert-butoxycarbonylamino-3-hydroxy-1-(6-methoxyquinol-4-yl)-1-triethylsilyloxy-hexane

acetic anhydride

(2R,3R)-2-tert-butoxycarbonylamino-3-(6-methoxyquinol-4-yl)-3-triethylsilyloxy-propanal

(2R,3R)-2-tert-Butoxycarbonylamino-3-(6-methoxy-quinolin-4-yl)-3-triethylsilanyloxy-propionic acid methyl ester

Downstream raw materials:

(2S,3S)-1-[(E)-4-benzoyloxy-2-butenyl]-2-[(R)-6-methoxyquinol-4-yl-triethylsilyloxy]methyl-3-trimethylsilyloxy-piperidine

Benzoic acid (E)-4-{(R)-6-[(R)-(6-methoxy-quinolin-4-yl)-triethylsilanyloxy-methyl]-5-trimethylsilanyloxy-3,6-dihydro-2H-pyridin-1-yl}-but-2-enyl ester

(R)-1-((E)-4-Benzoyloxy-but-2-enyl)-2-[(R)-(6-methoxy-quinolin-4-yl)-triethylsilanyloxy-methyl]-3-oxo-piperidine-4-carboxylic acid methyl ester

(2R)-1-[(E)-4-benzoyloxy-2-butenyl]-2-[(R)-6-methoxyquinol-4-yl-triethylsilyloxy]methyl-3-oxo-piperidine

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