2-benzylamino-1-O-2-N-carbonyl-2-deoxy-3,4-O-(1-methylethylidene)-5-O-tert-butyldiphenylsilyl-L-xylitol

Base Information

• Chemical Name: 2-benzylamino-1-O-2-N-carbonyl-2-deoxy-3,4-O-(1-methylethylidene)-5-O-tert-butyldiphenylsilyl-L-xylitol
• CAS No.: 133760-22-2
• Molecular Formula: C₃₂H₃₉NO₅Si
• Molecular Weight: 545.751
• Mol file: 133760-22-2.mol

Synonyms:2-benzylamino-1-O-2-N-carbonyl-2-deoxy-3,4-O-(1-methylethylidene)-5-O-tert-butyldiphenylsilyl-L-xylitol

Chemical Property of 2-benzylamino-1-O-2-N-carbonyl-2-deoxy-3,4-O-(1-methylethylidene)-5-O-tert-butyldiphenylsilyl-L-xylitol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2-benzylamino-1-O-2-N-carbonyl-2-deoxy-3,4-O-(1-methylethylidene)-5-O-tert-butyldiphenylsilyl-L-xylitol

There total 10 articles about 2-benzylamino-1-O-2-N-carbonyl-2-deoxy-3,4-O-(1-methylethylidene)-5-O-tert-butyldiphenylsilyl-L-xylitol 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: 64.0%

2-benzyl(benzyloxycarbonyl)amino-5-O-tert-butyldiphenylsilyl-2-deoxy-3,4-O-(1-methylethylidene)-L-xylose O-trifluoroacetyl S-phenyl monothioacetal (133760-33-5,133782-26-0) → 2-benzylamino-1-O-2-N-carbonyl-2-deoxy-3,4-O-(1-methylethylidene)-5-O-tert-butyldiphenylsilyl-L-xylitol (133760-22-2)

Guidance literature:

With sodium tetrahydroborate; In ethanol; at 0 ℃; for 2h;

DOI:10.1055/s-1991-26401

Reference yield:

2,3-O-isopropylidene-L-arabinose diethyl mercaptal (53872-72-3) → 2-benzylamino-1-O-2-N-carbonyl-2-deoxy-3,4-O-(1-methylethylidene)-5-O-tert-butyldiphenylsilyl-L-xylitol (133760-22-2)

Guidance literature:

Multi-step reaction with 10 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

10: 64 percent / NaBH₄ / ethanol / 2 h / 0 °C

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; ethanol; dichloromethane; water; N,N-dimethyl-formamide; acetone; toluene;

DOI:10.1055/s-1991-26401

Reference yield:

4,5-dideoxy-4,5-imino-2,3-O-(1-methylethylidene)-D-xylose diethyl dithioacetal (126448-15-5) → 2-benzylamino-1-O-2-N-carbonyl-2-deoxy-3,4-O-(1-methylethylidene)-5-O-tert-butyldiphenylsilyl-L-xylitol (133760-22-2)

Guidance literature:

Multi-step reaction with 8 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

8: 64 percent / NaBH₄ / ethanol / 2 h / 0 °C

With 1H-imidazole; 2,6-dimethylpyridine; sodium tetrahydroborate; iodine; sodium hydrogencarbonate; triethylamine; 3-chloro-benzenecarboperoxoic acid; In methanol; ethanol; dichloromethane; water; N,N-dimethyl-formamide; acetone;

DOI:10.1055/s-1991-26401

upstream raw materials:

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

2,3-O-isopropylidene-L-arabinose diethyl mercaptal

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

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