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

Base Information

Chemical Name:(2S,4S,5R)-4-<(2-acetamido-4-O-sulfo-3,6-di-O-benzyl-2-deoxy-β-D-glucopyranosyl)oxy>-5-<(benzyloxy)methyl>-1,2-pyrrolidinedicarboxylic acid bis(phenylmethyl ester)
CAS No.:132696-23-2
Molecular Formula:C₅₀H₅₃N₂O₁₄S*Na
Molecular Weight:961.032
Hs Code.:

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

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

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

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

There total 11 articles about (2S,4S,5R)-4-<(2-acetamido-4-O-sulfo-3,6-di-O-benzyl-2-deoxy-β-D-glucopyranosyl)oxy>-5-<(benzyloxy)methyl>-1,2-pyrrolidinedicarboxylic acid bis(phenylmethyl 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: 65.0%

: 129001-57-6
(2S,4S,5R)-4-<(2-acetamido-3,6-di-O-benzyl-2-deoxy-β-D-glucopyranosyl)oxy>-5-<(benzyloxy)methyl>-1,2-pyrrolidinedicarboxylic acid bis(phenylmethyl ester)

: 132696-23-2
(2S,4S,5R)-4-<(2-acetamido-4-O-sulfo-3,6-di-O-benzyl-2-deoxy-β-D-glucopyranosyl)oxy>-5-<(benzyloxy)methyl>-1,2-pyrrolidinedicarboxylic acid bis(phenylmethyl ester)

Guidance literature:: With sulfur trioxide pyridine complex; In N,N-dimethyl-formamide; Ambient temperature;
DOI:10.1021/jo00008a040

Reference yield:

: 120312-09-6
tert-Butyldimethylsilyl-2-azido-3,6-di-O-benzyl-2-desoxy-β-D-glucopyranosid

: 132696-23-2
(2S,4S,5R)-4-<(2-acetamido-4-O-sulfo-3,6-di-O-benzyl-2-deoxy-β-D-glucopyranosyl)oxy>-5-<(benzyloxy)methyl>-1,2-pyrrolidinedicarboxylic acid bis(phenylmethyl ester)

Guidance literature:: Multi-step reaction with 7 steps

1: 89 percent / Et₃N, DMAP / CH₂Cl₂ / 4 h / Ambient temperature

2: 96 percent / AcOH, Bu₄NF / tetrahydrofuran / 1 h / Ambient temperature

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

4: 59 percent / a) 4-A molecular sieves b) BF₃*Et₂O / CH₂Cl₂ / -40 °C / a) 3h, b) 45 min

5: 48 h / Ambient temperature

6: 74 percent / aq. KOH / methanol / Ambient temperature

7: 65 percent / pyridine*SO₃ / dimethylformamide / Ambient temperature

With dmap; potassium hydroxide; 4 A molecular sieve; tetrabutyl ammonium fluoride; sulfur trioxide pyridine complex; acetic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1021/jo00008a040

Reference yield:

: 100-39-0
benzyl bromide

: 132696-23-2
(2S,4S,5R)-4-<(2-acetamido-4-O-sulfo-3,6-di-O-benzyl-2-deoxy-β-D-glucopyranosyl)oxy>-5-<(benzyloxy)methyl>-1,2-pyrrolidinedicarboxylic acid bis(phenylmethyl ester)

Guidance literature:: Multi-step reaction with 10 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: 59 percent / a) 4-A molecular sieves b) BF₃*Et₂O / CH₂Cl₂ / -40 °C / a) 3h, b) 45 min

8: 48 h / Ambient temperature

9: 74 percent / aq. KOH / methanol / Ambient temperature

10: 65 percent / pyridine*SO₃ / dimethylformamide / Ambient temperature

With dmap; potassium hydroxide; 4 A molecular sieve; tetrabutyl ammonium fluoride; tetrabutylammomium bromide; sulfur trioxide pyridine complex; 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; methanol; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1021/jo00008a040