methyl 2,3-dideoxy-3-methoxycarbonylamino-6-O-toluenesulphonyl-2-trimethylsilylethylsulfonamido-α-D-altropyranoside

Base Information

Chemical Name:methyl 2,3-dideoxy-3-methoxycarbonylamino-6-O-toluenesulphonyl-2-trimethylsilylethylsulfonamido-α-D-altropyranoside
CAS No.:592527-22-5
Molecular Formula:C₂₁H₃₆N₂O₁₀S₂Si
Molecular Weight:568.742
Hs Code.:

Synonyms:methyl 2,3-dideoxy-3-methoxycarbonylamino-6-O-toluenesulphonyl-2-trimethylsilylethylsulfonamido-α-D-altropyranoside

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Chemical Property of methyl 2,3-dideoxy-3-methoxycarbonylamino-6-O-toluenesulphonyl-2-trimethylsilylethylsulfonamido-α-D-altropyranoside

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Technology Process of methyl 2,3-dideoxy-3-methoxycarbonylamino-6-O-toluenesulphonyl-2-trimethylsilylethylsulfonamido-α-D-altropyranoside

There total 7 articles about methyl 2,3-dideoxy-3-methoxycarbonylamino-6-O-toluenesulphonyl-2-trimethylsilylethylsulfonamido-α-D-altropyranoside 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: 79.0%

: 98-59-9
p-toluenesulfonyl chloride

: 592527-20-3
methyl 2,3-dideoxy-3-methoxycarbonylamino-2-trimethylsilylethylsulfonamido-α-D-altropyranoside

: 592527-22-5
methyl 2,3-dideoxy-3-methoxycarbonylamino-6-O-toluenesulphonyl-2-trimethylsilylethylsulfonamido-α-D-altropyranoside

Guidance literature:: With dmap; triethylamine; In dichloromethane; at 0 - 20 ℃;
DOI:10.1021/ol035036l

Reference yield:

: 71184-91-3
methyl 4,6-O-benzylidene-2,3-dideoxy-2,3-epimino-α-D-allopyranoside

: 592527-22-5
methyl 2,3-dideoxy-3-methoxycarbonylamino-6-O-toluenesulphonyl-2-trimethylsilylethylsulfonamido-α-D-altropyranoside

Guidance literature:: Multi-step reaction with 6 steps

1: 86 percent / pyridine / CH₂Cl₂ / 0 - 20 °C

2: 88 percent / NaN₃; NH₄Cl / dimethylformamide / 4 h / Heating

3: 95 percent / H₂ / Pd(OH)2/C / methanol / 3 h / 20 °C / 760 Torr

4: 61 percent / AgCN / benzene / 22 h / 75 °C

5: 85 percent / AcCl / methanol / 2.17 h / 0 - 20 °C

6: 79 percent / 4-dimethylaminopyridine; Et₃N / CH₂Cl₂ / 0 - 20 °C

With pyridine; dmap; sodium azide; silver cyanide; hydrogen; ammonium chloride; triethylamine; acetyl chloride; palladium dihydroxide; In methanol; dichloromethane; N,N-dimethyl-formamide; benzene; 2: Furst-Plattner ring-opening;
DOI:10.1021/ol035036l

Reference yield:

: 592527-09-8
methyl 4,6-O-benzylidene-2,3-dideoxy-2,3-(N-methoxycarbonyl)epimino-α-D-allopyranoside

: 592527-22-5
methyl 2,3-dideoxy-3-methoxycarbonylamino-6-O-toluenesulphonyl-2-trimethylsilylethylsulfonamido-α-D-altropyranoside

Guidance literature:: Multi-step reaction with 5 steps

1: 88 percent / NaN₃; NH₄Cl / dimethylformamide / 4 h / Heating

2: 95 percent / H₂ / Pd(OH)2/C / methanol / 3 h / 20 °C / 760 Torr

3: 61 percent / AgCN / benzene / 22 h / 75 °C

4: 85 percent / AcCl / methanol / 2.17 h / 0 - 20 °C

5: 79 percent / 4-dimethylaminopyridine; Et₃N / CH₂Cl₂ / 0 - 20 °C

With dmap; sodium azide; silver cyanide; hydrogen; ammonium chloride; triethylamine; acetyl chloride; palladium dihydroxide; In methanol; dichloromethane; N,N-dimethyl-formamide; benzene; 1: Furst-Plattner ring-opening;
DOI:10.1021/ol035036l