(2S,3S,4S,5R,6S)-3,4,5-Tris-benzyloxy-6-{4-[(2S,3R)-1-(4-methoxy-phenyl)-4-oxo-3-(3-phenyl-propyl)-azetidin-2-yl]-phenoxy}-tetrahydro-pyran-2-carboxylic acid benzyl ester

Base Information

• Chemical Name: (2S,3S,4S,5R,6S)-3,4,5-Tris-benzyloxy-6-{4-[(2S,3R)-1-(4-methoxy-phenyl)-4-oxo-3-(3-phenyl-propyl)-azetidin-2-yl]-phenoxy}-tetrahydro-pyran-2-carboxylic acid benzyl ester
• CAS No.: 190448-74-9
• Molecular Formula: C₅₉H₅₇NO₉
• Molecular Weight: 924.103

Synonyms:(2S,3S,4S,5R,6S)-3,4,5-Tris-benzyloxy-6-{4-[(2S,3R)-1-(4-methoxy-phenyl)-4-oxo-3-(3-phenyl-propyl)-azetidin-2-yl]-phenoxy}-tetrahydro-pyran-2-carboxylic acid benzyl ester

Chemical Property of (2S,3S,4S,5R,6S)-3,4,5-Tris-benzyloxy-6-{4-[(2S,3R)-1-(4-methoxy-phenyl)-4-oxo-3-(3-phenyl-propyl)-azetidin-2-yl]-phenoxy}-tetrahydro-pyran-2-carboxylic acid benzyl ester

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Technology Process of (2S,3S,4S,5R,6S)-3,4,5-Tris-benzyloxy-6-{4-[(2S,3R)-1-(4-methoxy-phenyl)-4-oxo-3-(3-phenyl-propyl)-azetidin-2-yl]-phenoxy}-tetrahydro-pyran-2-carboxylic acid benzyl ester

There total 7 articles about (2S,3S,4S,5R,6S)-3,4,5-Tris-benzyloxy-6-{4-[(2S,3R)-1-(4-methoxy-phenyl)-4-oxo-3-(3-phenyl-propyl)-azetidin-2-yl]-phenoxy}-tetrahydro-pyran-2-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: 60.0%

2,3,4-tri-O-benzyl-D-glucopyranosideuronic acid benzyl ester (4539-78-0) + (3R,4S)-4-(4-Hydroxy-phenyl)-1-(4-methoxy-phenyl)-3-(3-phenyl-propyl)-azetidin-2-one (175415-07-3) → (2S,3S,4S,5R,6S)-3,4,5-Tris-benzyloxy-6-{4-[(2S,3R)-1-(4-methoxy-phenyl)-4-oxo-3-(3-phenyl-propyl)-azetidin-2-yl]-phenoxy}-tetrahydro-pyran-2-carboxylic acid benzyl ester (190448-74-9)

Guidance literature:

With tributylphosphine; 1,1'-azodicarbonyl-dipiperidine; In tetrahydrofuran; at 0 - 20 ℃;

DOI:10.1016/S0960-894X(97)10185-8

Reference yield:

(4-Benzyloxybenzylidene)-(4-methoxyphenyl)amine → (2S,3S,4S,5R,6S)-3,4,5-Tris-benzyloxy-6-{4-[(2S,3R)-1-(4-methoxy-phenyl)-4-oxo-3-(3-phenyl-propyl)-azetidin-2-yl]-phenoxy}-tetrahydro-pyran-2-carboxylic acid benzyl ester (190448-74-9)

Guidance literature:

Multi-step reaction with 5 steps

1: 1.) TiCl₄, DIPEA / 1.) CH₂Cl₂, 2.) CH₂Cl₂

2: toluene / 90 °C

3: TBAF

4: 92 percent / H₂ / 10percent Pd/C / ethyl acetate; methanol / 3102.9 Torr

5: 60 percent / 1,1'-(azodicarbonyl)dipiperidine, Bu₃P / tetrahydrofuran / 0 - 20 °C

With tributylphosphine; tetrabutyl ammonium fluoride; hydrogen; titanium tetrachloride; N-ethyl-N,N-diisopropylamine; 1,1'-azodicarbonyl-dipiperidine; palladium on activated charcoal; In tetrahydrofuran; methanol; ethyl acetate; toluene;

DOI:10.1016/S0960-894X(97)10185-8

Reference yield:

(S)-4-Phenyl-3-(5-phenyl-pentanoyl)-oxazolidin-2-one (157435-14-8) → (2S,3S,4S,5R,6S)-3,4,5-Tris-benzyloxy-6-{4-[(2S,3R)-1-(4-methoxy-phenyl)-4-oxo-3-(3-phenyl-propyl)-azetidin-2-yl]-phenoxy}-tetrahydro-pyran-2-carboxylic acid benzyl ester (190448-74-9)

Guidance literature:

Multi-step reaction with 5 steps

1: 1.) TiCl₄, DIPEA / 1.) CH₂Cl₂, 2.) CH₂Cl₂

2: toluene / 90 °C

3: TBAF

4: 92 percent / H₂ / 10percent Pd/C / ethyl acetate; methanol / 3102.9 Torr

5: 60 percent / 1,1'-(azodicarbonyl)dipiperidine, Bu₃P / tetrahydrofuran / 0 - 20 °C

With tributylphosphine; tetrabutyl ammonium fluoride; hydrogen; titanium tetrachloride; N-ethyl-N,N-diisopropylamine; 1,1'-azodicarbonyl-dipiperidine; palladium on activated charcoal; In tetrahydrofuran; methanol; ethyl acetate; toluene;

DOI:10.1016/S0960-894X(97)10185-8

upstream raw materials:

2,3,4-tri-O-benzyl-D-glucopyranosideuronic acid benzyl ester

(3R,4S)-4-(4-Hydroxy-phenyl)-1-(4-methoxy-phenyl)-3-(3-phenyl-propyl)-azetidin-2-one

(S)-4-Phenyl-3-(5-phenyl-pentanoyl)-oxazolidin-2-one

(3R,4S)-4-(4-Benzyloxy-phenyl)-1-(4-methoxy-phenyl)-3-(3-phenyl-propyl)-azetidin-2-one

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