benzyl-[6-(3,4-bis-benzyloxy-5-{4-benzyloxy-5-(1-benzyloxy-ethyl)-3-[(2,5-dioxo-pyrrolidin-1-yl)-(4-methoxy-phenyl)-methoxy]-tetrahydro-furan-2-yloxy}-6-benzyloxymethyl-tetrahydro-pyran-2-yloxy)-hexyl]-carbamic acid benzyl ester

Base Information

• Chemical Name: benzyl-[6-(3,4-bis-benzyloxy-5-{4-benzyloxy-5-(1-benzyloxy-ethyl)-3-[(2,5-dioxo-pyrrolidin-1-yl)-(4-methoxy-phenyl)-methoxy]-tetrahydro-furan-2-yloxy}-6-benzyloxymethyl-tetrahydro-pyran-2-yloxy)-hexyl]-carbamic acid benzyl ester
• CAS No.: 571201-39-3
• Molecular Formula: C₈₀H₈₈N₂O₁₅
• Molecular Weight: 1317.58

Synonyms:

Chemical Property of benzyl-[6-(3,4-bis-benzyloxy-5-{4-benzyloxy-5-(1-benzyloxy-ethyl)-3-[(2,5-dioxo-pyrrolidin-1-yl)-(4-methoxy-phenyl)-methoxy]-tetrahydro-furan-2-yloxy}-6-benzyloxymethyl-tetrahydro-pyran-2-yloxy)-hexyl]-carbamic acid benzyl ester

Chemical Property:

Purity/Quality:

Safty Information:

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MSDS Files:

Useful:

Technology Process of benzyl-[6-(3,4-bis-benzyloxy-5-{4-benzyloxy-5-(1-benzyloxy-ethyl)-3-[(2,5-dioxo-pyrrolidin-1-yl)-(4-methoxy-phenyl)-methoxy]-tetrahydro-furan-2-yloxy}-6-benzyloxymethyl-tetrahydro-pyran-2-yloxy)-hexyl]-carbamic acid benzyl ester

There total 11 articles about benzyl-[6-(3,4-bis-benzyloxy-5-{4-benzyloxy-5-(1-benzyloxy-ethyl)-3-[(2,5-dioxo-pyrrolidin-1-yl)-(4-methoxy-phenyl)-methoxy]-tetrahydro-furan-2-yloxy}-6-benzyloxymethyl-tetrahydro-pyran-2-yloxy)-hexyl]-carbamic 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:

D-Galactose (10257-28-0) → benzyl-[6-(3,4-bis-benzyloxy-5-{4-benzyloxy-5-(1-benzyloxy-ethyl)-3-[(2,5-dioxo-pyrrolidin-1-yl)-(4-methoxy-phenyl)-methoxy]-tetrahydro-furan-2-yloxy}-6-benzyloxymethyl-tetrahydro-pyran-2-yloxy)-hexyl]-carbamic acid benzyl ester (571201-39-3)

Guidance literature:

Multi-step reaction with 9 steps

1.1: NaH; sodium iodide / various solvent(s) / 120 h / 20 °C

1.2: Pyr / various solvent(s) / 24 h / 0 °C

2.1: 2.01 g / MeONa / methanol

3.1: 75 percent / DMAP / pyridine / 2 h

4.1: 77 percent / triethylamine; DMAP / tetrahydrofuran / 1 h / 0 °C

5.1: TBAI; NaH / CH₂Cl₂ / 120 h / Heating

5.2: 85 percent / IR resin (H+ form) / CH₂Cl₂ / 1 h / pH 1

6.1: 94 percent / Et₃N; DMAP / CH₂Cl₂ / 4 h / Heating

7.1: NaBH₄ / dimethylformamide / 44 h / 20 °C

7.2: 77 percent / MeONa / methanol; dimethylformamide / 2 h / 20 °C

8.1: DDQ / CH₂Cl₂ / 1 h / 20 °C

9.1: CH₂Cl₂ / 19 h / 20 °C

With dmap; sodium tetrahydroborate; sodium methylate; tetra-(n-butyl)ammonium iodide; sodium hydride; triethylamine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; sodium iodide; In tetrahydrofuran; pyridine; methanol; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1002/ejoc.200390184

Reference yield:

p-methoxybenzyl chloride (824-94-2) → benzyl-[6-(3,4-bis-benzyloxy-5-{4-benzyloxy-5-(1-benzyloxy-ethyl)-3-[(2,5-dioxo-pyrrolidin-1-yl)-(4-methoxy-phenyl)-methoxy]-tetrahydro-furan-2-yloxy}-6-benzyloxymethyl-tetrahydro-pyran-2-yloxy)-hexyl]-carbamic acid benzyl ester (571201-39-3)

Guidance literature:

Multi-step reaction with 3 steps

1: 90 percent / NaH / dimethylformamide / 1.5 h / 20 °C

2: DDQ / CH₂Cl₂ / 1 h / 20 °C

3: CH₂Cl₂ / 19 h / 20 °C

With sodium hydride; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In dichloromethane; N,N-dimethyl-formamide;

DOI:10.1002/ejoc.200390184

Reference yield:

pent-4-enyl 2,3,5,6-tetra-O-acetyl-α-D-galactofuranoside (172975-17-6) → benzyl-[6-(3,4-bis-benzyloxy-5-{4-benzyloxy-5-(1-benzyloxy-ethyl)-3-[(2,5-dioxo-pyrrolidin-1-yl)-(4-methoxy-phenyl)-methoxy]-tetrahydro-furan-2-yloxy}-6-benzyloxymethyl-tetrahydro-pyran-2-yloxy)-hexyl]-carbamic acid benzyl ester (571201-39-3)

Guidance literature:

Multi-step reaction with 8 steps

1.1: 2.01 g / MeONa / methanol

2.1: 75 percent / DMAP / pyridine / 2 h

3.1: 77 percent / triethylamine; DMAP / tetrahydrofuran / 1 h / 0 °C

4.1: TBAI; NaH / CH₂Cl₂ / 120 h / Heating

4.2: 85 percent / IR resin (H+ form) / CH₂Cl₂ / 1 h / pH 1

5.1: 94 percent / Et₃N; DMAP / CH₂Cl₂ / 4 h / Heating

6.1: NaBH₄ / dimethylformamide / 44 h / 20 °C

6.2: 77 percent / MeONa / methanol; dimethylformamide / 2 h / 20 °C

7.1: DDQ / CH₂Cl₂ / 1 h / 20 °C

8.1: CH₂Cl₂ / 19 h / 20 °C

With dmap; sodium tetrahydroborate; sodium methylate; tetra-(n-butyl)ammonium iodide; sodium hydride; triethylamine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In tetrahydrofuran; pyridine; methanol; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1002/ejoc.200390184

upstream raw materials:

N-iodo-succinimide

Benzyl-(6-{(2R,3R,4S,5S,6R)-3,4-bis-benzyloxy-5-[[(2S,3R,4S,5S)-4-benzyloxy-5-((R)-1-benzyloxy-ethyl)-2-pent-4-enyloxy-tetrahydro-furan-3-yloxy]-(4-methoxy-phenyl)-methoxy]-6-benzyloxymethyl-tetrahydro-pyran-2-yloxy}-hexyl)-carbamic acid benzyl ester

D-Galactose

p-methoxybenzyl chloride

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