(2S,4S,5R)-4-<(2-acetamido-3,6-di-O-benzyl-2-deoxy-β-D-glucopyranosyl)oxy>-5-<(benzyloxy)methyl>-1,2-pyrrolidinedicarboxylic acid 1-(phenylmethyl) monoester

Base Information

Chemical Name:(2S,4S,5R)-4-<(2-acetamido-3,6-di-O-benzyl-2-deoxy-β-D-glucopyranosyl)oxy>-5-<(benzyloxy)methyl>-1,2-pyrrolidinedicarboxylic acid 1-(phenylmethyl) monoester
CAS No.:132592-38-2
Molecular Formula:C₄₃H₄₈N₂O₁₁
Molecular Weight:768.861
Hs Code.:

(2S,4S,5R)-4-<(2-acetamido-3,6-di-O-benzyl-2-deoxy-β-D-glucopyranosyl)oxy>-5-<(benzyloxy)methyl>-1,2-pyrrolidinedicarboxylic acid 1-(phenylmethyl) monoester

Synonyms:(2S,4S,5R)-4-<(2-acetamido-3,6-di-O-benzyl-2-deoxy-β-D-glucopyranosyl)oxy>-5-<(benzyloxy)methyl>-1,2-pyrrolidinedicarboxylic acid 1-(phenylmethyl) monoester

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Chemical Property of (2S,4S,5R)-4-<(2-acetamido-3,6-di-O-benzyl-2-deoxy-β-D-glucopyranosyl)oxy>-5-<(benzyloxy)methyl>-1,2-pyrrolidinedicarboxylic acid 1-(phenylmethyl) monoester

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Technology Process of (2S,4S,5R)-4-<(2-acetamido-3,6-di-O-benzyl-2-deoxy-β-D-glucopyranosyl)oxy>-5-<(benzyloxy)methyl>-1,2-pyrrolidinedicarboxylic acid 1-(phenylmethyl) monoester

There total 29 articles about (2S,4S,5R)-4-<(2-acetamido-3,6-di-O-benzyl-2-deoxy-β-D-glucopyranosyl)oxy>-5-<(benzyloxy)methyl>-1,2-pyrrolidinedicarboxylic acid 1-(phenylmethyl) monoester 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%

: C₄₆H₅₂N₂O₁₂

: 132592-38-2
(2S,4S,5R)-4-<(2-acetamido-3,6-di-O-benzyl-2-deoxy-β-D-glucopyranosyl)oxy>-5-<(benzyloxy)methyl>-1,2-pyrrolidinedicarboxylic acid 1-(phenylmethyl) monoester

Guidance literature:: With potassium hydroxide; In water; isopropyl alcohol; for 72h;
DOI:10.1021/acsinfecdis.8b00105

Reference yield:

: 100-39-0
benzyl bromide

: 132592-38-2
(2S,4S,5R)-4-<(2-acetamido-3,6-di-O-benzyl-2-deoxy-β-D-glucopyranosyl)oxy>-5-<(benzyloxy)methyl>-1,2-pyrrolidinedicarboxylic acid 1-(phenylmethyl) monoester

Guidance literature:: Multi-step reaction with 9 steps

1: 84 percent / Bu₄NI, NaH / tetrahydrofuran / 5 h / 0 deg C to r.t.

2: 74 percent / TFA / tetrahydrofuran / 0.25 h / 0 °C

3: 1) (Bu₃Sn)2O, 2) Bu₄NBr / 1) toluene, reflux, 4h, 2) 80 deg C

4: 89 percent / Et₃N, DMAP / CH₂Cl₂ / 4 h / Ambient temperature

5: 96 percent / AcOH, Bu₄NF / tetrahydrofuran / 1 h / Ambient temperature

6: 1) 4A molecular sieves, 2) DBU / 1) CH₂Cl₂,r.t., 4h, 2) -40 deg C, 3h

7: 42 percent / a) 4-A molecular sieves b) BF₃*Et₂O / CH₂Cl₂ / -40 °C / a) 4h, b) 50 min

8: 80 percent / 24 h / Ambient temperature

9: aq. KOH / propan-2-ol / 96 h

With dmap; potassium hydroxide; 4 A molecular sieve; tetrabutyl ammonium fluoride; tetrabutylammomium bromide; tetra-(n-butyl)ammonium iodide; sodium hydride; acetic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; trifluoroacetic acid; bis(tri-n-butyltin)oxide; In tetrahydrofuran; dichloromethane; isopropyl alcohol;
DOI:10.1021/jo00008a040

Reference yield:

: 132592-31-5
(5R,4S,2S)-4-acetoxy-5-(hydroxymethyl)-1,2-pyrrolidinedicarboxylic acid 2-methyl 1-(phenylmethyl) diester

: 132592-38-2
(2S,4S,5R)-4-<(2-acetamido-3,6-di-O-benzyl-2-deoxy-β-D-glucopyranosyl)oxy>-5-<(benzyloxy)methyl>-1,2-pyrrolidinedicarboxylic acid 1-(phenylmethyl) monoester

Guidance literature:: Multi-step reaction with 5 steps

1: 91 percent / Ag₂O / CH₂Cl₂ / Heating; a) 10h, b) 12h

2: 100 percent / NaOMe / methanol / 1 h / Ambient temperature

3: 42 percent / a) 4-A molecular sieves b) BF₃*Et₂O / CH₂Cl₂ / -40 °C / a) 4h, b) 50 min

4: 80 percent / 24 h / Ambient temperature

5: aq. KOH / propan-2-ol / 96 h

With potassium hydroxide; 4 A molecular sieve; sodium methylate; silver(l) oxide; In methanol; dichloromethane; isopropyl alcohol;
DOI:10.1021/jo00008a040