benzyl 2-acetamido-4-O-<2-acetamido-3-O-benzyl-2-deoxy-4,6-O-isopropylidene-β-D-glucopyranosyl>-6-O-benzyl-2-deoxy-3-O-(D-2-propanoyl-L-alanyl-D-isoglutamine benzyl ester)-α-D-glucopyranoside

Base Information

• Chemical Name: benzyl 2-acetamido-4-O-<2-acetamido-3-O-benzyl-2-deoxy-4,6-O-isopropylidene-β-D-glucopyranosyl>-6-O-benzyl-2-deoxy-3-O-(D-2-propanoyl-L-alanyl-D-isoglutamine benzyl ester)-α-D-glucopyranoside
• CAS No.: 75957-48-1
• Molecular Formula: C₅₈H₇₃N₅O₁₆
• Molecular Weight: 1096.24

Synonyms:benzyl 2-acetamido-4-O-<2-acetamido-3-O-benzyl-2-deoxy-4,6-O-isopropylidene-β-D-glucopyranosyl>-6-O-benzyl-2-deoxy-3-O-(D-2-propanoyl-L-alanyl-D-isoglutamine benzyl ester)-α-D-glucopyranoside

Chemical Property of benzyl 2-acetamido-4-O-<2-acetamido-3-O-benzyl-2-deoxy-4,6-O-isopropylidene-β-D-glucopyranosyl>-6-O-benzyl-2-deoxy-3-O-(D-2-propanoyl-L-alanyl-D-isoglutamine benzyl ester)-α-D-glucopyranoside

Chemical Property:

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Technology Process of benzyl 2-acetamido-4-O-<2-acetamido-3-O-benzyl-2-deoxy-4,6-O-isopropylidene-β-D-glucopyranosyl>-6-O-benzyl-2-deoxy-3-O-(D-2-propanoyl-L-alanyl-D-isoglutamine benzyl ester)-α-D-glucopyranoside

There total 13 articles about benzyl 2-acetamido-4-O-<2-acetamido-3-O-benzyl-2-deoxy-4,6-O-isopropylidene-β-D-glucopyranosyl>-6-O-benzyl-2-deoxy-3-O-(D-2-propanoyl-L-alanyl-D-isoglutamine benzyl ester)-α-D-glucopyranoside 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:

N-((4aR,6S,7R,8R,8aS)-6-(benzyloxy)-8-hydroxy-2,2-dimethylhexahydropyrano[3,2-d][1,3]dioxin-7-yl)acetamide (66026-10-6) → benzyl 2-acetamido-4-O-<2-acetamido-3-O-benzyl-2-deoxy-4,6-O-isopropylidene-β-D-glucopyranosyl>-6-O-benzyl-2-deoxy-3-O-(D-2-propanoyl-L-alanyl-D-isoglutamine benzyl ester)-α-D-glucopyranoside (75957-48-1)

Guidance literature:

Multi-step reaction with 12 steps

1: 76.4 percent / barium oxide, barium hydroxide octahydrate / dimethylformamide / 36 h / 0 - 22 °C

2: 96.4 percent / 60percent acetic acid / H₂O / 3 h / 60 °C

3: 82 percent / pyridine / 1 h / -20 °C

4: p-TsOH*H₂O / dioxane / 3 h / Ambient temperature

5: 1.) barium oxide, barium hydroxide octahydrate; 2.) 70percent acetic acid / 1.) N,N-dimethylformamide, 0 deg C, room temperature, 18 h; 2.) water, 50 deg C, 4 h

6: 36.1 percent / p-TsOH / 1,2-dichloro-ethane / 10 h / Heating

7: 467 mg / sodium methoxide / methanol

8: 384 mg / p-TsOH*H₂O / dimethylformamide / 2 h / 50 °C

9: 1.) barium oxide, barium hydroxide octahydrate; 2.) 70percent acetic acid / 1.) N,N-dimethylformamide, room temperature, 18 h; 2.) water, 50 deg C, 4 h

10: 76.2 percent / potassium tert-butoxide / dimethylsulfoxide / 4 h / 50 °C

11: 1.) sodium hydride / 1.) 1,4-dioxane, 95 deg C, 1.5 h; 2.) 1,4-dioxane, 65 deg C, 3 h

12: 1.) N-hydroxylsuccinimide, dicyclohexylcarbodiimide; 2.) triethylamine / 1.) 1,4-dioxane, room temperature, 2.5 h; 2.) 1,4-dioxane, room temperature, 2 h

With pyridine; 1-hydroxy-pyrrolidine-2,5-dione; barium hydroxide octahydrate; potassium tert-butylate; sodium methylate; sodium hydride; toluene-4-sulfonic acid; acetic acid; triethylamine; dicyclohexyl-carbodiimide; barium(II) oxide; In 1,4-dioxane; methanol; water; dimethyl sulfoxide; 1,2-dichloro-ethane; N,N-dimethyl-formamide;

DOI:10.1016/S0008-6215(00)82587-2

Reference yield:

N-{(2S,3R,4R,5S,6R)-2-Benzyloxy-4-[((E)-but-2-enyl)oxy]-5-hydroxy-6-hydroxymethyl-tetrahydro-pyran-3-yl}-acetamide (83100-64-5) → benzyl 2-acetamido-4-O-<2-acetamido-3-O-benzyl-2-deoxy-4,6-O-isopropylidene-β-D-glucopyranosyl>-6-O-benzyl-2-deoxy-3-O-(D-2-propanoyl-L-alanyl-D-isoglutamine benzyl ester)-α-D-glucopyranoside (75957-48-1)

Guidance literature:

Multi-step reaction with 10 steps

1: 82 percent / pyridine / 1 h / -20 °C

2: p-TsOH*H₂O / dioxane / 3 h / Ambient temperature

3: 1.) barium oxide, barium hydroxide octahydrate; 2.) 70percent acetic acid / 1.) N,N-dimethylformamide, 0 deg C, room temperature, 18 h; 2.) water, 50 deg C, 4 h

4: 36.1 percent / p-TsOH / 1,2-dichloro-ethane / 10 h / Heating

5: 467 mg / sodium methoxide / methanol

6: 384 mg / p-TsOH*H₂O / dimethylformamide / 2 h / 50 °C

7: 1.) barium oxide, barium hydroxide octahydrate; 2.) 70percent acetic acid / 1.) N,N-dimethylformamide, room temperature, 18 h; 2.) water, 50 deg C, 4 h

8: 76.2 percent / potassium tert-butoxide / dimethylsulfoxide / 4 h / 50 °C

9: 1.) sodium hydride / 1.) 1,4-dioxane, 95 deg C, 1.5 h; 2.) 1,4-dioxane, 65 deg C, 3 h

10: 1.) N-hydroxylsuccinimide, dicyclohexylcarbodiimide; 2.) triethylamine / 1.) 1,4-dioxane, room temperature, 2.5 h; 2.) 1,4-dioxane, room temperature, 2 h

With pyridine; 1-hydroxy-pyrrolidine-2,5-dione; barium hydroxide octahydrate; potassium tert-butylate; sodium methylate; sodium hydride; toluene-4-sulfonic acid; acetic acid; triethylamine; dicyclohexyl-carbodiimide; barium(II) oxide; In 1,4-dioxane; methanol; dimethyl sulfoxide; 1,2-dichloro-ethane; N,N-dimethyl-formamide;

DOI:10.1016/S0008-6215(00)82587-2

Reference yield:

benzyl 2-acetamido-3-O-(2-butenyl)-2-deoxy-4,6-O-isopropylidene-α-D-glucopyranoside (83100-63-4) → benzyl 2-acetamido-4-O-<2-acetamido-3-O-benzyl-2-deoxy-4,6-O-isopropylidene-β-D-glucopyranosyl>-6-O-benzyl-2-deoxy-3-O-(D-2-propanoyl-L-alanyl-D-isoglutamine benzyl ester)-α-D-glucopyranoside (75957-48-1)

Guidance literature:

Multi-step reaction with 11 steps

1: 96.4 percent / 60percent acetic acid / H₂O / 3 h / 60 °C

2: 82 percent / pyridine / 1 h / -20 °C

3: p-TsOH*H₂O / dioxane / 3 h / Ambient temperature

4: 1.) barium oxide, barium hydroxide octahydrate; 2.) 70percent acetic acid / 1.) N,N-dimethylformamide, 0 deg C, room temperature, 18 h; 2.) water, 50 deg C, 4 h

5: 36.1 percent / p-TsOH / 1,2-dichloro-ethane / 10 h / Heating

6: 467 mg / sodium methoxide / methanol

7: 384 mg / p-TsOH*H₂O / dimethylformamide / 2 h / 50 °C

8: 1.) barium oxide, barium hydroxide octahydrate; 2.) 70percent acetic acid / 1.) N,N-dimethylformamide, room temperature, 18 h; 2.) water, 50 deg C, 4 h

9: 76.2 percent / potassium tert-butoxide / dimethylsulfoxide / 4 h / 50 °C

10: 1.) sodium hydride / 1.) 1,4-dioxane, 95 deg C, 1.5 h; 2.) 1,4-dioxane, 65 deg C, 3 h

11: 1.) N-hydroxylsuccinimide, dicyclohexylcarbodiimide; 2.) triethylamine / 1.) 1,4-dioxane, room temperature, 2.5 h; 2.) 1,4-dioxane, room temperature, 2 h

With pyridine; 1-hydroxy-pyrrolidine-2,5-dione; barium hydroxide octahydrate; potassium tert-butylate; sodium methylate; sodium hydride; toluene-4-sulfonic acid; acetic acid; triethylamine; dicyclohexyl-carbodiimide; barium(II) oxide; In 1,4-dioxane; methanol; water; dimethyl sulfoxide; 1,2-dichloro-ethane; N,N-dimethyl-formamide;

DOI:10.1016/S0008-6215(00)82587-2

upstream raw materials:

(S)-1-(((R)-1-amino-5-(benzyloxy)-1,5-dioxopentan-2-yl)amino)-1-oxopropan-2-aminium 2,2,2-trifluoroacetate

benzyl 2-acetamido-4-O-(2-acetamido-3-O-benzyl-2-deoxy-4,6-O-isopropylidene-β-D-glucopyranosyl)-6-O-benzyl-3-O-(D-1-carboxyethyl)-α-D-glucopyranoside

N-((4aR,6S,7R,8R,8aS)-6-(benzyloxy)-8-hydroxy-2,2-dimethylhexahydropyrano[3,2-d][1,3]dioxin-7-yl)acetamide

N-{(2S,3R,4R,5S,6R)-2-Benzyloxy-4-[((E)-but-2-enyl)oxy]-5-hydroxy-6-hydroxymethyl-tetrahydro-pyran-3-yl}-acetamide

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