(3R,5R,6S)-3-[(S)-3-((3S,5S,6R)-4-Benzyloxycarbonyl-2-oxo-5,6-diphenyl-morpholin-3-yl)-3-phenoxythiocarbonyloxy-propyl]-3-methoxymethyl-2-oxo-5,6-diphenyl-morpholine-4-carboxylic acid benzyl ester

Base Information

Chemical Name:(3R,5R,6S)-3-[(S)-3-((3S,5S,6R)-4-Benzyloxycarbonyl-2-oxo-5,6-diphenyl-morpholin-3-yl)-3-phenoxythiocarbonyloxy-propyl]-3-methoxymethyl-2-oxo-5,6-diphenyl-morpholine-4-carboxylic acid benzyl ester
CAS No.:135560-78-0
Molecular Formula:C₆₀H₅₄N₂O₁₁S
Molecular Weight:1011.16
Hs Code.:

(3R,5R,6S)-3-[(S)-3-((3S,5S,6R)-4-Benzyloxycarbonyl-2-oxo-5,6-diphenyl-morpholin-3-yl)-3-phenoxythiocarbonyloxy-propyl]-3-methoxymethyl-2-oxo-5,6-diphenyl-morpholine-4-carboxylic acid benzyl ester

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Chemical Property of (3R,5R,6S)-3-[(S)-3-((3S,5S,6R)-4-Benzyloxycarbonyl-2-oxo-5,6-diphenyl-morpholin-3-yl)-3-phenoxythiocarbonyloxy-propyl]-3-methoxymethyl-2-oxo-5,6-diphenyl-morpholine-4-carboxylic acid benzyl ester

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Technology Process of (3R,5R,6S)-3-[(S)-3-((3S,5S,6R)-4-Benzyloxycarbonyl-2-oxo-5,6-diphenyl-morpholin-3-yl)-3-phenoxythiocarbonyloxy-propyl]-3-methoxymethyl-2-oxo-5,6-diphenyl-morpholine-4-carboxylic acid benzyl ester

There total 10 articles about (3R,5R,6S)-3-[(S)-3-((3S,5S,6R)-4-Benzyloxycarbonyl-2-oxo-5,6-diphenyl-morpholin-3-yl)-3-phenoxythiocarbonyloxy-propyl]-3-methoxymethyl-2-oxo-5,6-diphenyl-morpholine-4-carboxylic acid benzyl ester 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: 62.0%

: 135560-77-9,135636-80-5,135636-82-7,135636-83-8,135636-87-2,135636-88-3
(3R,5R,6S)-3-[(S)-3-((3S,5S,6R)-4-Benzyloxycarbonyl-2-oxo-5,6-diphenyl-morpholin-3-yl)-3-hydroxy-propyl]-3-methoxymethyl-2-oxo-5,6-diphenyl-morpholine-4-carboxylic acid benzyl ester

: 1005-56-7
phenylcarbonochloridothioate

: 135560-78-0,135636-84-9
(3R,5R,6S)-3-[(S)-3-((3S,5S,6R)-4-Benzyloxycarbonyl-2-oxo-5,6-diphenyl-morpholin-3-yl)-3-phenoxythiocarbonyloxy-propyl]-3-methoxymethyl-2-oxo-5,6-diphenyl-morpholine-4-carboxylic acid benzyl ester

Guidance literature:: With sodium hexamethyldisilazane; In tetrahydrofuran; 1.) -78 deg C, 10 min, 2.) 3 h;
DOI:10.1021/ja00018a040

Reference yield: 38.0%

: 135560-77-9,135636-80-5,135636-82-7,135636-83-8,135636-87-2,135636-88-3
(3S,5S,6R)-3-[(S)-3-((3S,5S,6R)-4-Benzyloxycarbonyl-2-oxo-5,6-diphenyl-morpholin-3-yl)-3-hydroxy-propyl]-3-methoxymethyl-2-oxo-5,6-diphenyl-morpholine-4-carboxylic acid benzyl ester

: 1005-56-7
phenylcarbonochloridothioate

: 135560-78-0,135636-84-9
(3S,5S,6R)-3-[(S)-3-((3S,5S,6R)-4-Benzyloxycarbonyl-2-oxo-5,6-diphenyl-morpholin-3-yl)-3-phenoxythiocarbonyloxy-propyl]-3-methoxymethyl-2-oxo-5,6-diphenyl-morpholine-4-carboxylic acid benzyl ester

Guidance literature:: With sodium hexamethyldisilazane; In tetrahydrofuran; at -78 ℃; for 3h;
DOI:10.1021/ja00018a040

Reference yield:

: 100516-54-9,335159-14-3
(5S,6R)-4-(benzyloxycarbonyl)-5,6-diphenyl-2,3,5,6-tetrahydro-4H-1,4-oxazin-2-one

: 135560-78-0,135636-84-9
(3S,5S,6R)-3-[(S)-3-((3S,5S,6R)-4-Benzyloxycarbonyl-2-oxo-5,6-diphenyl-morpholin-3-yl)-3-phenoxythiocarbonyloxy-propyl]-3-methoxymethyl-2-oxo-5,6-diphenyl-morpholine-4-carboxylic acid benzyl ester

Guidance literature:: Multi-step reaction with 5 steps

1: 48.5 percent / HMPA, lithium bis(trimethylsilyl)amide / tetrahydrofuran / 1.) -78 deg C, 10 min, 2.) 1 h

2: 88.5 percent / potassium bis(trimethylsilyl)amide / tetrahydrofuran / 0.83 h / -78 °C

3: 94 percent / ozone / methanol; CH₂Cl₂ / 0.08 h

4: 1.) dibutylboron triflate, triethylamine / 1.) CH₂Cl₂, 0 deg C, 20 min, 2.) CH₂Cl₂, -78 deg C, 30 min

5: 38 percent / sodium bis(trimethylsilyl)amide / tetrahydrofuran / 3 h / -78 °C

With N,N,N,N,N,N-hexamethylphosphoric triamide; di-n-butylboryl trifluoromethanesulfonate; sodium hexamethyldisilazane; potassium hexamethylsilazane; ozone; triethylamine; lithium hexamethyldisilazane; In tetrahydrofuran; methanol; dichloromethane;
DOI:10.1021/ja00018a040