(4,8-anhydro-2,3-di-O-benzyl-6,7-dideoxy-8S-C-phenyl-β-D-manno-octopyranosyl)-(1→3)-1,2:5,6-di-O-isopropylidene-α-D-glucofuranose

Base Information

• Chemical Name: (4,8-anhydro-2,3-di-O-benzyl-6,7-dideoxy-8S-C-phenyl-β-D-manno-octopyranosyl)-(1→3)-1,2:5,6-di-O-isopropylidene-α-D-glucofuranose
• CAS No.: 1421832-86-1
• Molecular Formula: C₄₀H₄₈O₁₀
• Molecular Weight: 688.815
• Mol file: 1421832-86-1.mol

Synonyms:

Chemical Property of (4,8-anhydro-2,3-di-O-benzyl-6,7-dideoxy-8S-C-phenyl-β-D-manno-octopyranosyl)-(1→3)-1,2:5,6-di-O-isopropylidene-α-D-glucofuranose

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (4,8-anhydro-2,3-di-O-benzyl-6,7-dideoxy-8S-C-phenyl-β-D-manno-octopyranosyl)-(1→3)-1,2:5,6-di-O-isopropylidene-α-D-glucofuranose

There total 15 articles about (4,8-anhydro-2,3-di-O-benzyl-6,7-dideoxy-8S-C-phenyl-β-D-manno-octopyranosyl)-(1→3)-1,2:5,6-di-O-isopropylidene-α-D-glucofuranose 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:

phenylthio 4,8-anhydro-2,3-di-O-benzyl-6,7-dideoxy-8S-phenyl-α-D-manno-octopyranoside (1421832-81-6) + 1,2:5,6-di-O-isopropylidene-α-D-glucofuranose (582-52-5) → (4,8-anhydro-2,3-di-O-benzyl-6,7-dideoxy-8S-C-phenyl-α-D-manno-octopyranosyl)-(1→3)-1,2:5,6-di-O-isopropylidene-α-D-glucofuranose (1421832-84-9) + (4,8-anhydro-2,3-di-O-benzyl-6,7-dideoxy-8S-C-phenyl-β-D-manno-octopyranosyl)-(1→3)-1,2:5,6-di-O-isopropylidene-α-D-glucofuranose (1421832-86-1)

Guidance literature:

phenylthio 4,8-anhydro-2,3-di-O-benzyl-6,7-dideoxy-8S-phenyl-α-D-manno-octopyranoside; With 1-benzenesulfinyl piperidine; 2,4,6-tri-tert-butylpyrimidine; In dichloromethane; at -60 ℃; for 1h; Molecular sieve; Inert atmosphere;

With trifluoromethylsulfonic anhydride; In dichloromethane; at -60 ℃; for 0.5h; Molecular sieve; Inert atmosphere;

1,2:5,6-di-O-isopropylidene-α-D-glucofuranose; In dichloromethane; at -60 ℃; Overall yield = 43 %; stereoselective reaction; Inert atmosphere; Molecular sieve;

DOI:10.1021/jo302455d

Reference yield:

phenyl 2,3-di-O-benzyl-1-thio-α-D-mannopyranoside (449761-78-8) → (4,8-anhydro-2,3-di-O-benzyl-6,7-dideoxy-8S-C-phenyl-α-D-manno-octopyranosyl)-(1→3)-1,2:5,6-di-O-isopropylidene-α-D-glucofuranose (1421832-84-9) + (4,8-anhydro-2,3-di-O-benzyl-6,7-dideoxy-8S-C-phenyl-β-D-manno-octopyranosyl)-(1→3)-1,2:5,6-di-O-isopropylidene-α-D-glucofuranose (1421832-86-1)

Guidance literature:

Multi-step reaction with 8 steps

1.1: pyridine; dmap / 23 h / 20 °C / Inert atmosphere

1.2: 6.5 h / 20 °C / Inert atmosphere

2.1: trifluoroacetic acid; trifluoroacetic anhydride / dichloromethane / 4 °C / Inert atmosphere

3.1: Dess-Martin periodane / dichloromethane / 22 h / 20 °C / Inert atmosphere

4.1: dichloromethane / 22 h / 20 °C / Inert atmosphere

5.1: (triphenylphosphine)copper(I) hydride hexamer; water / benzene / 0.5 h / Schlenk technique; Inert atmosphere

6.1: sodium methylate; methanol / tetrahydrofuran / 144 h / 20 °C / Inert atmosphere

7.1: Amberlite IR-120H / methanol; tetrahydrofuran / 48 h / 20 °C / Inert atmosphere

7.2: Inert atmosphere; Cooling with ice

8.1: 2,4,6-tri-tert-butylpyrimidine; 1-benzenesulfinyl piperidine / dichloromethane / 1 h / -60 °C / Molecular sieve; Inert atmosphere

8.2: 0.5 h / -60 °C / Molecular sieve; Inert atmosphere

8.3: -60 °C / Inert atmosphere; Molecular sieve

With pyridine; methanol; dmap; (triphenylphosphine)copper(I) hydride hexamer; 1-benzenesulfinyl piperidine; water; sodium methylate; Dess-Martin periodane; trifluoroacetic acid; trifluoroacetic anhydride; 2,4,6-tri-tert-butylpyrimidine; In tetrahydrofuran; methanol; dichloromethane; benzene; 3.1: |Dess-Martin Oxidation;

DOI:10.1021/jo302455d

Reference yield:

phenyl 2,3-di-O-benzyl-4,6-O-benzylidene-1-deoxy-1-thio-α-D-mannopyranoside → (4,8-anhydro-2,3-di-O-benzyl-6,7-dideoxy-8S-C-phenyl-α-D-manno-octopyranosyl)-(1→3)-1,2:5,6-di-O-isopropylidene-α-D-glucofuranose (1421832-84-9) + (4,8-anhydro-2,3-di-O-benzyl-6,7-dideoxy-8S-C-phenyl-β-D-manno-octopyranosyl)-(1→3)-1,2:5,6-di-O-isopropylidene-α-D-glucofuranose (1421832-86-1)

Guidance literature:

Multi-step reaction with 10 steps

1.1: toluene-4-sulfonic acid / dichloromethane; methanol / 18 h / 20 °C / Inert atmosphere

2.1: 1H-imidazole / N,N-dimethyl-formamide / 3 h / 0 - 20 °C / Inert atmosphere

3.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 1.5 h / Inert atmosphere; Cooling

4.1: tetrabutyl ammonium fluoride / dichloromethane; tetrahydrofuran / 18 h / Inert atmosphere

5.1: Dess-Martin periodane / dichloromethane / 5.5 h / Inert atmosphere

6.1: dichloromethane / 13 h / Inert atmosphere

7.1: (triphenylphosphine)copper(I) hydride hexamer; water / benzene / 0.5 h / Schlenk technique; Inert atmosphere

8.1: water; 2,3-dicyano-5,6-dichloro-p-benzoquinone / dichloromethane / 2 h

9.1: Amberlite IR-120H / methanol; tetrahydrofuran / 48 h / 20 °C / Inert atmosphere

9.2: Inert atmosphere; Cooling with ice

10.1: 2,4,6-tri-tert-butylpyrimidine; 1-benzenesulfinyl piperidine / dichloromethane / 1 h / -60 °C / Molecular sieve; Inert atmosphere

10.2: 0.5 h / -60 °C / Molecular sieve; Inert atmosphere

10.3: -60 °C / Inert atmosphere; Molecular sieve

With 1H-imidazole; (triphenylphosphine)copper(I) hydride hexamer; 1-benzenesulfinyl piperidine; tetrabutyl ammonium fluoride; water; sodium hydride; Dess-Martin periodane; toluene-4-sulfonic acid; 2,3-dicyano-5,6-dichloro-p-benzoquinone; 2,4,6-tri-tert-butylpyrimidine; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; mineral oil; benzene; 5.1: |Dess-Martin Oxidation / 6.1: |Wittig Olefination;

DOI:10.1021/jo302455d

upstream raw materials:

phenylthio 4-O-benzoyl-2,3-di-O-benzyl-6-O-trityl-α-D-mannopyranoside

phenylthio 2,3-di-O-benzyl-4-O-benzoyl-α-D-mannopyranoside

(E)-phenylthio 4-O-benzoyl-2,3-di-O-benzyl-6,7-dideoxy-8-C-phenyl-α-D-manno-oct-6-eno-8-ulo-pyranoside

phenyl 2,3-di-O-benzyl-1-thio-α-D-mannopyranoside