phenyl 4,7-di-O-benzyl-3-O-tert-butyldimethylsilyl-6-deoxy-2-O-(2-naphthylmethyl)-1-thio-α-D-manno-heptopyranoside

Base Information

Chemical Name:phenyl 4,7-di-O-benzyl-3-O-tert-butyldimethylsilyl-6-deoxy-2-O-(2-naphthylmethyl)-1-thio-α-D-manno-heptopyranoside
CAS No.:1607006-01-8
Molecular Formula:C₄₄H₅₂O₅SSi
Molecular Weight:721.045
Hs Code.:

Synonyms:phenyl 4,7-di-O-benzyl-3-O-tert-butyldimethylsilyl-6-deoxy-2-O-(2-naphthylmethyl)-1-thio-α-D-manno-heptopyranoside

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Chemical Property of phenyl 4,7-di-O-benzyl-3-O-tert-butyldimethylsilyl-6-deoxy-2-O-(2-naphthylmethyl)-1-thio-α-D-manno-heptopyranoside

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Technology Process of phenyl 4,7-di-O-benzyl-3-O-tert-butyldimethylsilyl-6-deoxy-2-O-(2-naphthylmethyl)-1-thio-α-D-manno-heptopyranoside

There total 8 articles about phenyl 4,7-di-O-benzyl-3-O-tert-butyldimethylsilyl-6-deoxy-2-O-(2-naphthylmethyl)-1-thio-α-D-manno-heptopyranoside 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:

: 69739-34-0
t-butyldimethylsiyl triflate

: 1607006-01-8
phenyl 4,7-di-O-benzyl-3-O-tert-butyldimethylsilyl-6-deoxy-2-O-(2-naphthylmethyl)-1-thio-α-D-manno-heptopyranoside

Guidance literature:: Multi-step reaction with 8 steps

1.1: triethylamine / N,N-dimethyl-formamide / 2 h / -10 °C / Inert atmosphere

2.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 0.33 h / Cooling with ice; Inert atmosphere

2.2: 3 h / 20 °C / Inert atmosphere

3.1: borane-THF; trimethylsilyl trifluoromethanesulfonate / tetrahydrofuran; dichloromethane / 3 h / 23 °C / Inert atmosphere

4.1: pyridine; dmap / 20 h / 0 °C / Inert atmosphere

5.1: 18-crown-6 ether / acetonitrile / 24.5 h / 0.22 - 20 °C / Molecular sieve; Inert atmosphere

6.1: diisobutylaluminium hydride / toluene / 0.25 h / -78 °C / Inert atmosphere

6.2: 1 h / 20 °C / Inert atmosphere

7.1: sodium tetrahydroborate / methanol; dichloromethane / 1 h / 20 °C / Inert atmosphere

8.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 0.5 h / 0 °C / Inert atmosphere

8.2: 20 h / 20 °C / Inert atmosphere

With pyridine; dmap; sodium tetrahydroborate; borane-THF; 18-crown-6 ether; trimethylsilyl trifluoromethanesulfonate; sodium hydride; diisobutylaluminium hydride; triethylamine; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; toluene; acetonitrile; mineral oil;
DOI:10.1021/jo500640n

Reference yield:

: 1250346-19-0
phenyl 4,6-O-benzylidene-3-O-tert-butyldimethylsilyl-2-O-(2-naphthylmethyl)-1-thio-α-D-mannopyranoside

: 1607006-38-1
C₃₈H₃₈O₅S

: 1607006-01-8
phenyl 4,7-di-O-benzyl-3-O-tert-butyldimethylsilyl-6-deoxy-2-O-(2-naphthylmethyl)-1-thio-α-D-manno-heptopyranoside

Guidance literature:: Multi-step reaction with 6 steps

1.1: borane-THF; scandium tris(trifluoromethanesulfonate) / tetrahydrofuran; dichloromethane / 21 h / 23 °C / Inert atmosphere

2.1: pyridine; dmap / 20 h / 0 °C / Inert atmosphere

3.1: 18-crown-6 ether / acetonitrile / 24.5 h / 0.22 - 20 °C / Molecular sieve; Inert atmosphere

4.1: diisobutylaluminium hydride / toluene / 0.25 h / -78 °C / Inert atmosphere

4.2: 1 h / 20 °C / Inert atmosphere

5.1: sodium tetrahydroborate / methanol; dichloromethane / 1 h / 20 °C / Inert atmosphere

6.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 0.5 h / 0 °C / Inert atmosphere

6.2: 20 h / 20 °C / Inert atmosphere

With pyridine; dmap; sodium tetrahydroborate; borane-THF; 18-crown-6 ether; sodium hydride; diisobutylaluminium hydride; scandium tris(trifluoromethanesulfonate); In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; toluene; acetonitrile; mineral oil;
DOI:10.1021/jo500640n

Reference yield:

: 922183-00-4
phenyl 4,6-O-benzylidene-3-O-tert-butyldimethylsilyl-1-thio-α-D-mannopyranoside

: 1607006-38-1
C₃₈H₃₈O₅S

: 1607006-01-8
phenyl 4,7-di-O-benzyl-3-O-tert-butyldimethylsilyl-6-deoxy-2-O-(2-naphthylmethyl)-1-thio-α-D-manno-heptopyranoside

Guidance literature:: Multi-step reaction with 7 steps

1.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 0.33 h / Cooling with ice; Inert atmosphere

1.2: 3 h / 20 °C / Inert atmosphere

2.1: borane-THF; scandium tris(trifluoromethanesulfonate) / tetrahydrofuran; dichloromethane / 21 h / 23 °C / Inert atmosphere

3.1: pyridine; dmap / 20 h / 0 °C / Inert atmosphere

4.1: 18-crown-6 ether / acetonitrile / 24.5 h / 0.22 - 20 °C / Molecular sieve; Inert atmosphere

5.1: diisobutylaluminium hydride / toluene / 0.25 h / -78 °C / Inert atmosphere

5.2: 1 h / 20 °C / Inert atmosphere

6.1: sodium tetrahydroborate / methanol; dichloromethane / 1 h / 20 °C / Inert atmosphere

7.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 0.5 h / 0 °C / Inert atmosphere

7.2: 20 h / 20 °C / Inert atmosphere

With pyridine; dmap; sodium tetrahydroborate; borane-THF; 18-crown-6 ether; sodium hydride; diisobutylaluminium hydride; scandium tris(trifluoromethanesulfonate); In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; toluene; acetonitrile; mineral oil;
DOI:10.1021/jo500640n