(R)-N-[(2R,3R,4S,5R,6R)-3,4-Diacetoxy-6-acetoxymethyl-5-((2S,3R,4S,5S,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-2-yl]-2-(1,3-dioxo-1,3-dihydro-isoindol-2-yloxy)-succinamic acid benzyl ester

Base Information

• Chemical Name: (R)-N-[(2R,3R,4S,5R,6R)-3,4-Diacetoxy-6-acetoxymethyl-5-((2S,3R,4S,5S,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-2-yl]-2-(1,3-dioxo-1,3-dihydro-isoindol-2-yloxy)-succinamic acid benzyl ester
• CAS No.: 309730-54-9
• Molecular Formula: C₄₅H₅₀N₂O₂₃
• Molecular Weight: 986.892
• Mol file: 309730-54-9.mol

Synonyms:(R)-N-[(2R,3R,4S,5R,6R)-3,4-Diacetoxy-6-acetoxymethyl-5-((2S,3R,4S,5S,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-2-yl]-2-(1,3-dioxo-1,3-dihydro-isoindol-2-yloxy)-succinamic acid benzyl ester

Chemical Property of (R)-N-[(2R,3R,4S,5R,6R)-3,4-Diacetoxy-6-acetoxymethyl-5-((2S,3R,4S,5S,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-2-yl]-2-(1,3-dioxo-1,3-dihydro-isoindol-2-yloxy)-succinamic acid benzyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (R)-N-[(2R,3R,4S,5R,6R)-3,4-Diacetoxy-6-acetoxymethyl-5-((2S,3R,4S,5S,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-2-yl]-2-(1,3-dioxo-1,3-dihydro-isoindol-2-yloxy)-succinamic acid benzyl ester

There total 4 articles about (R)-N-[(2R,3R,4S,5R,6R)-3,4-Diacetoxy-6-acetoxymethyl-5-((2S,3R,4S,5S,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-2-yl]-2-(1,3-dioxo-1,3-dihydro-isoindol-2-yloxy)-succinamic 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: 82.0%

N-hydroxyphthalimide (524-38-9) + Benzyl (S)-2-hydroxy-N-(2,3,6-tri-O-acetyl-4-O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-β-D-glucopyranosyl)succinate (309730-49-2) → (R)-N-[(2R,3R,4S,5R,6R)-3,4-Diacetoxy-6-acetoxymethyl-5-((2S,3R,4S,5S,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-2-yl]-2-(1,3-dioxo-1,3-dihydro-isoindol-2-yloxy)-succinamic acid benzyl ester (309730-54-9)

Guidance literature:

With di-isopropyl azodicarboxylate; triphenylphosphine; In dichloromethane; at -20 ℃; for 3h;

Reference yield:

2,3,6-tri-O-acetyl-4-O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-β-D-glucopyranosylamine (59044-96-1,93079-64-2,120575-75-9,30854-63-8) → (R)-N-[(2R,3R,4S,5R,6R)-3,4-Diacetoxy-6-acetoxymethyl-5-((2S,3R,4S,5S,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-2-yl]-2-(1,3-dioxo-1,3-dihydro-isoindol-2-yloxy)-succinamic acid benzyl ester (309730-54-9)

Guidance literature:

Multi-step reaction with 3 steps

1: 99 percent / HBTU; i-Pr₂NEt / dimethylformamide

2: 85 percent / BF₃*OEt₂ / CHCl₃ / 1.5 h / 20 °C

3: 82 percent / PPh₃; DIAD / CH₂Cl₂ / 3 h / -20 °C

With di-isopropyl azodicarboxylate; boron trifluoride diethyl etherate; O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine; triphenylphosphine; In dichloromethane; chloroform; N,N-dimethyl-formamide; 1: glycosylation / 2: desilylation / 3: Mitsunobu reaction;

Reference yield:

benzyl hydrogen (S)-2-(tert-butyldimethylsilyloxy)succinate (309730-43-6) → (R)-N-[(2R,3R,4S,5R,6R)-3,4-Diacetoxy-6-acetoxymethyl-5-((2S,3R,4S,5S,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-2-yl]-2-(1,3-dioxo-1,3-dihydro-isoindol-2-yloxy)-succinamic acid benzyl ester (309730-54-9)

Guidance literature:

Multi-step reaction with 3 steps

1: 99 percent / HBTU; i-Pr₂NEt / dimethylformamide

2: 85 percent / BF₃*OEt₂ / CHCl₃ / 1.5 h / 20 °C

3: 82 percent / PPh₃; DIAD / CH₂Cl₂ / 3 h / -20 °C

With di-isopropyl azodicarboxylate; boron trifluoride diethyl etherate; O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine; triphenylphosphine; In dichloromethane; chloroform; N,N-dimethyl-formamide; 1: glycosylation / 2: desilylation / 3: Mitsunobu reaction;

upstream raw materials:

N-hydroxyphthalimide

Benzyl (S)-2-hydroxy-N-(2,3,6-tri-O-acetyl-4-O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-β-D-glucopyranosyl)succinate

2,3,6-tri-O-acetyl-4-O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-β-D-glucopyranosylamine

benzyl hydrogen (S)-2-(tert-butyldimethylsilyloxy)succinate