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

Base Information

• Chemical Name: Benzyl (S)-2-tert-butyldimethylsilyloxy-N-(2,3,6-tri-O-acetyl-4-O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-β-D-glucopyranosyl)succinate
• CAS No.: 309730-46-9
• Molecular Formula: C₄₃H₆₁NO₂₁Si
• Molecular Weight: 956.037
• Mol file: 309730-46-9.mol

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

Chemical Property of Benzyl (S)-2-tert-butyldimethylsilyloxy-N-(2,3,6-tri-O-acetyl-4-O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-β-D-glucopyranosyl)succinate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Benzyl (S)-2-tert-butyldimethylsilyloxy-N-(2,3,6-tri-O-acetyl-4-O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-β-D-glucopyranosyl)succinate

There total 1 articles about Benzyl (S)-2-tert-butyldimethylsilyloxy-N-(2,3,6-tri-O-acetyl-4-O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-β-D-glucopyranosyl)succinate 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: 99.0%

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) + benzyl hydrogen (S)-2-(tert-butyldimethylsilyloxy)succinate (309730-43-6) → Benzyl (S)-2-tert-butyldimethylsilyloxy-N-(2,3,6-tri-O-acetyl-4-O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-β-D-glucopyranosyl)succinate (309730-46-9)

Guidance literature:

With O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide;

Reference yield: 85.0%

Benzyl (S)-2-tert-butyldimethylsilyloxy-N-(2,3,6-tri-O-acetyl-4-O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-β-D-glucopyranosyl)succinate (309730-46-9) → 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)

Guidance literature:

With boron trifluoride diethyl etherate; In chloroform; at 20 ℃; for 1.5h;

Reference yield:

Benzyl (S)-2-tert-butyldimethylsilyloxy-N-(2,3,6-tri-O-acetyl-4-O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-β-D-glucopyranosyl)succinate (309730-46-9) → (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 2 steps

1: 85 percent / BF₃*OEt₂ / CHCl₃ / 1.5 h / 20 °C

2: 82 percent / PPh₃; DIAD / CH₂Cl₂ / 3 h / -20 °C

With di-isopropyl azodicarboxylate; boron trifluoride diethyl etherate; triphenylphosphine; In dichloromethane; chloroform; 1: desilylation / 2: Mitsunobu reaction;

upstream raw materials:

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

Downstream raw materials:

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

(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