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

Base Information

Chemical Name:(1R,2S,3R)-6-benzyloxy-2-tert-butoxycarbonylamino-3-hydroxy-1-(6-methoxyquinol-4-yl)-1-triethylsilyloxy-hexane
CAS No.:911319-45-4
Molecular Formula:C₃₄H₅₀N₂O₆Si
Molecular Weight:610.866
Hs Code.:

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

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

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

There total 10 articles about (1R,2S,3R)-6-benzyloxy-2-tert-butoxycarbonylamino-3-hydroxy-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: 87.0%

: 911319-65-8
(2R,3R)-2-tert-butoxycarbonylamino-3-(6-methoxyquinol-4-yl)-3-triethylsilyloxy-propanal

: 54314-84-0
1-[(3-bromopropoxy)methyl]-benzene

: 911319-45-4
(1R,2S,3R)-6-benzyloxy-2-tert-butoxycarbonylamino-3-hydroxy-1-(6-methoxyquinol-4-yl)-1-triethylsilyloxy-hexane

Guidance literature:: 1-[(3-bromopropoxy)methyl]-benzene; With iodine; magnesium; In diethyl ether; at 20 ℃; for 1h;

(2R,3R)-2-tert-butoxycarbonylamino-3-(6-methoxyquinol-4-yl)-3-triethylsilyloxy-propanal; In tetrahydrofuran; diethyl ether; at -78 ℃; for 0.25h;
DOI:10.1021/ol061524s

Reference yield:

: 911319-42-1
(3R,5R,6S)-3-[(R)-Hydroxy-(6-methoxy-quinolin-4-yl)-methyl]-2-oxo-5,6-diphenyl-morpholine-4-carboxylic acid benzyl ester

: 911319-45-4
(1R,2S,3R)-6-benzyloxy-2-tert-butoxycarbonylamino-3-hydroxy-1-(6-methoxyquinol-4-yl)-1-triethylsilyloxy-hexane

Guidance literature:: Multi-step reaction with 6 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

With lead(IV) acetate; dmap; hydrogen; iodine; diisobutylaluminium hydride; magnesium; zinc(II) chloride; palladium on activated charcoal; In tetrahydrofuran; methanol; diethyl ether; hexane; dichloromethane; ethyl acetate; toluene;
DOI:10.1021/ol061524s

Reference yield:

: 911319-43-2
(3R,5R,6S)-3-[(R)-(6-Methoxy-quinolin-4-yl)-triethylsilanyloxy-methyl]-2-oxo-5,6-diphenyl-morpholine-4-carboxylic acid benzyl ester

: 911319-45-4
(1R,2S,3R)-6-benzyloxy-2-tert-butoxycarbonylamino-3-hydroxy-1-(6-methoxyquinol-4-yl)-1-triethylsilyloxy-hexane

Guidance literature:: Multi-step reaction with 5 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

With lead(IV) acetate; hydrogen; iodine; diisobutylaluminium hydride; magnesium; zinc(II) chloride; palladium on activated charcoal; In methanol; diethyl ether; hexane; dichloromethane; ethyl acetate; toluene;
DOI:10.1021/ol061524s