2-benzyl(benzyloxycarbonyl)amino-5-O-tert-butyldiphenylsilyl-2-deoxy-3,4-O-(1-methylethylidene)-L-xylose O-trifluoroacetyl S-phenyl monothioacetal

Base Information

Chemical Name:2-benzyl(benzyloxycarbonyl)amino-5-O-tert-butyldiphenylsilyl-2-deoxy-3,4-O-(1-methylethylidene)-L-xylose O-trifluoroacetyl S-phenyl monothioacetal
CAS No.:133760-33-5
Molecular Formula:C₄₇H₅₀F₃NO₇SSi
Molecular Weight:858.063
Hs Code.:

2-benzyl(benzyloxycarbonyl)amino-5-O-tert-butyldiphenylsilyl-2-deoxy-3,4-O-(1-methylethylidene)-L-xylose O-trifluoroacetyl S-phenyl monothioacetal

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Chemical Property of 2-benzyl(benzyloxycarbonyl)amino-5-O-tert-butyldiphenylsilyl-2-deoxy-3,4-O-(1-methylethylidene)-L-xylose O-trifluoroacetyl S-phenyl monothioacetal

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Technology Process of 2-benzyl(benzyloxycarbonyl)amino-5-O-tert-butyldiphenylsilyl-2-deoxy-3,4-O-(1-methylethylidene)-L-xylose O-trifluoroacetyl S-phenyl monothioacetal

There total 9 articles about 2-benzyl(benzyloxycarbonyl)amino-5-O-tert-butyldiphenylsilyl-2-deoxy-3,4-O-(1-methylethylidene)-L-xylose O-trifluoroacetyl S-phenyl monothioacetal 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:

: 53872-72-3
2,3-O-isopropylidene-L-arabinose diethyl mercaptal

: 133760-33-5,133782-26-0
2-benzyl(benzyloxycarbonyl)amino-5-O-tert-butyldiphenylsilyl-2-deoxy-3,4-O-(1-methylethylidene)-L-xylose O-trifluoroacetyl S-phenyl monothioacetal

Guidance literature:: Multi-step reaction with 9 steps

1: 1) tosyl chloride, pyridine, 2) NaN₃ / 1) -5 deg C, 4 h, 2) DMF, 65 deg C, 3 h

2: PPh₃ / toluene / 1) 40 deg C, 30 min, 2) 100 deg C, 1 h

3: NEt₃ / CH₂Cl₂ / 2 h / Ambient temperature

5: NaHCO₃, I₂ / acetone; H₂O / 48 h

6: NaBH₄ / methanol / 2 h / 0 °C

7: 97 percent / imidazole / dimethylformamide / 3 h / Ambient temperature

8: 85 percent / MCPBA / CH₂Cl₂ / 2 h / 0 °C

9: 2,6-lutidine / CH₂Cl₂ / 1) 1 h, 0 deg C, 2) 1 h, RT

With pyridine; 1H-imidazole; 2,6-dimethylpyridine; sodium tetrahydroborate; sodium azide; iodine; sodium hydrogencarbonate; triethylamine; p-toluenesulfonyl chloride; 3-chloro-benzenecarboperoxoic acid; triphenylphosphine; In methanol; dichloromethane; water; N,N-dimethyl-formamide; acetone; toluene;
DOI:10.1055/s-1991-26401

Reference yield:

: 126448-15-5
4,5-dideoxy-4,5-imino-2,3-O-(1-methylethylidene)-D-xylose diethyl dithioacetal

: 133760-33-5,133782-26-0
2-benzyl(benzyloxycarbonyl)amino-5-O-tert-butyldiphenylsilyl-2-deoxy-3,4-O-(1-methylethylidene)-L-xylose O-trifluoroacetyl S-phenyl monothioacetal

Guidance literature:: Multi-step reaction with 7 steps

1: NEt₃ / CH₂Cl₂ / 2 h / Ambient temperature

3: NaHCO₃, I₂ / acetone; H₂O / 48 h

4: NaBH₄ / methanol / 2 h / 0 °C

5: 97 percent / imidazole / dimethylformamide / 3 h / Ambient temperature

6: 85 percent / MCPBA / CH₂Cl₂ / 2 h / 0 °C

7: 2,6-lutidine / CH₂Cl₂ / 1) 1 h, 0 deg C, 2) 1 h, RT

With 1H-imidazole; 2,6-dimethylpyridine; sodium tetrahydroborate; iodine; sodium hydrogencarbonate; triethylamine; 3-chloro-benzenecarboperoxoic acid; In methanol; dichloromethane; water; N,N-dimethyl-formamide; acetone;
DOI:10.1055/s-1991-26401

Reference yield:

: 126448-07-5
(S)-2-Azido-1-[(4S,5R)-5-(bis-ethylsulfanyl-methyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-ethanol

: 133760-33-5,133782-26-0
2-benzyl(benzyloxycarbonyl)amino-5-O-tert-butyldiphenylsilyl-2-deoxy-3,4-O-(1-methylethylidene)-L-xylose O-trifluoroacetyl S-phenyl monothioacetal

Guidance literature:: Multi-step reaction with 8 steps

1: PPh₃ / toluene / 1) 40 deg C, 30 min, 2) 100 deg C, 1 h

2: NEt₃ / CH₂Cl₂ / 2 h / Ambient temperature

4: NaHCO₃, I₂ / acetone; H₂O / 48 h

5: NaBH₄ / methanol / 2 h / 0 °C

6: 97 percent / imidazole / dimethylformamide / 3 h / Ambient temperature

7: 85 percent / MCPBA / CH₂Cl₂ / 2 h / 0 °C

8: 2,6-lutidine / CH₂Cl₂ / 1) 1 h, 0 deg C, 2) 1 h, RT

With 1H-imidazole; 2,6-dimethylpyridine; sodium tetrahydroborate; iodine; sodium hydrogencarbonate; triethylamine; 3-chloro-benzenecarboperoxoic acid; triphenylphosphine; In methanol; dichloromethane; water; N,N-dimethyl-formamide; acetone; toluene;
DOI:10.1055/s-1991-26401