1-adamantanyl 4,8-anhydro-2,3-di-O-benzyl-6,7-dideoxy-8S-phenyl-β-D-manno-octopyranoside

Base Information

Chemical Name:1-adamantanyl 4,8-anhydro-2,3-di-O-benzyl-6,7-dideoxy-8S-phenyl-β-D-manno-octopyranoside
CAS No.:1421832-83-8
Molecular Formula:C₃₈H₄₄O₅
Molecular Weight:580.764
Hs Code.:

Synonyms:

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Chemical Property of 1-adamantanyl 4,8-anhydro-2,3-di-O-benzyl-6,7-dideoxy-8S-phenyl-β-D-manno-octopyranoside

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Technology Process of 1-adamantanyl 4,8-anhydro-2,3-di-O-benzyl-6,7-dideoxy-8S-phenyl-β-D-manno-octopyranoside

There total 15 articles about 1-adamantanyl 4,8-anhydro-2,3-di-O-benzyl-6,7-dideoxy-8S-phenyl-β-D-manno-octopyranoside 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:

: 768-95-6
1-adamanthanol

: 1421832-81-6
phenylthio 4,8-anhydro-2,3-di-O-benzyl-6,7-dideoxy-8S-phenyl-α-D-manno-octopyranoside

: 1421832-82-7
1-adamantanyl 4,8-anhydro-2,3-di-O-benzyl-6,7-dideoxy-8S-phenyl-α-D-manno-octopyranoside

: 1421832-83-8
1-adamantanyl 4,8-anhydro-2,3-di-O-benzyl-6,7-dideoxy-8S-phenyl-β-D-manno-octopyranoside

Guidance literature:: 1-adamanthanol; phenylthio 4,8-anhydro-2,3-di-O-benzyl-6,7-dideoxy-8S-phenyl-α-D-manno-octopyranoside; In dichloromethane; at 0 ℃; for 1h; Molecular sieve; Inert atmosphere;

With N-iodo-succinimide; trifluorormethanesulfonic acid; In dichloromethane; at 0 ℃; Overall yield = 62 %; stereoselective reaction; Molecular sieve; Inert atmosphere;
DOI:10.1021/jo302455d

Reference yield:

: 449761-78-8
phenyl 2,3-di-O-benzyl-1-thio-α-D-mannopyranoside

: 1421832-82-7
1-adamantanyl 4,8-anhydro-2,3-di-O-benzyl-6,7-dideoxy-8S-phenyl-α-D-manno-octopyranoside

: 1421832-83-8
1-adamantanyl 4,8-anhydro-2,3-di-O-benzyl-6,7-dideoxy-8S-phenyl-β-D-manno-octopyranoside

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

: 1421832-82-7
1-adamantanyl 4,8-anhydro-2,3-di-O-benzyl-6,7-dideoxy-8S-phenyl-α-D-manno-octopyranoside

: 1421832-83-8
1-adamantanyl 4,8-anhydro-2,3-di-O-benzyl-6,7-dideoxy-8S-phenyl-β-D-manno-octopyranoside

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