2-benzyloxycarbonylamino-5-O-tert-butyldiphenylsilyl-2-deoxy-3,4-O-(1-methylethylidene)-L-xylonic acid

Base Information

• Chemical Name: 2-benzyloxycarbonylamino-5-O-tert-butyldiphenylsilyl-2-deoxy-3,4-O-(1-methylethylidene)-L-xylonic acid
• CAS No.: 126448-12-2
• Molecular Formula: C₃₂H₃₉NO₇Si
• Molecular Weight: 577.75

Synonyms:2-benzyloxycarbonylamino-5-O-tert-butyldiphenylsilyl-2-deoxy-3,4-O-(1-methylethylidene)-L-xylonic acid

Chemical Property of 2-benzyloxycarbonylamino-5-O-tert-butyldiphenylsilyl-2-deoxy-3,4-O-(1-methylethylidene)-L-xylonic acid

Chemical Property:

Purity/Quality:

98% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2-benzyloxycarbonylamino-5-O-tert-butyldiphenylsilyl-2-deoxy-3,4-O-(1-methylethylidene)-L-xylonic acid

There total 21 articles about 2-benzyloxycarbonylamino-5-O-tert-butyldiphenylsilyl-2-deoxy-3,4-O-(1-methylethylidene)-L-xylonic acid 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: 90.0%

2-benzyloxycarbonylamino-5-O-tert-butyldiphenylsilyl-2-deoxy-3,4-O-(1-methylethylidene)-L-xylitol (133760-23-3) → 2-benzyloxycarbonylamino-5-O-tert-butyldiphenylsilyl-2-deoxy-3,4-O-(1-methylethylidene)-L-xylonic acid (126448-12-2)

Guidance literature:

With sodium periodate; RuCl * H₂O; In tetrachloromethane; acetonitrile; for 2h; Ambient temperature;

DOI:10.1055/s-1991-26401

Reference yield:

2,3-O-isopropylidene-L-arabinose diethyl mercaptal (53872-72-3) → 2-benzyloxycarbonylamino-5-O-tert-butyldiphenylsilyl-2-deoxy-3,4-O-(1-methylethylidene)-L-xylonic acid (126448-12-2)

Guidance literature:

Multi-step reaction with 11 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

4: 85 percent / 1) NaH / tetrahydrofuran / 1) RT, 30 min, 2) RT, 4 h

5: NaHCO₃, I₂ / acetone; H₂O / 48 h / Ambient temperature

6: NaBH₄ / methanol / 3 h / 20 °C

7: 98 percent / imidazole / dimethylformamide / 3 h / Ambient temperature

8: 85 percent / MCPBA / CH₂Cl₂ / 1.5 h / 0 °C

9: 1) (CF₃CO)2O, 2) 2,6-lutidine / 1) overnight, RT, 2) 4 h, RT

10: 82 percent / NaBH₄ / methanol / 2 h / Ambient temperature

11: 90 percent / NaIO₄ / RuCl * H₂O / CCl₄; acetonitrile / 2 h / Ambient temperature

With pyridine; 1H-imidazole; 2,6-dimethylpyridine; sodium tetrahydroborate; sodium periodate; sodium azide; iodine; sodium hydride; sodium hydrogencarbonate; triethylamine; p-toluenesulfonyl chloride; 3-chloro-benzenecarboperoxoic acid; triphenylphosphine; trifluoroacetic anhydride; RuCl * H₂O; In tetrahydrofuran; methanol; tetrachloromethane; dichloromethane; water; N,N-dimethyl-formamide; acetone; toluene; acetonitrile;

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-benzyloxycarbonylamino-5-O-tert-butyldiphenylsilyl-2-deoxy-3,4-O-(1-methylethylidene)-L-xylonic acid (126448-12-2)

Guidance literature:

Multi-step reaction with 9 steps

1: NEt₃ / CH₂Cl₂ / 2 h / Ambient temperature

2: 85 percent / 1) NaH / tetrahydrofuran / 1) RT, 30 min, 2) RT, 4 h

3: NaHCO₃, I₂ / acetone; H₂O / 48 h / Ambient temperature

4: NaBH₄ / methanol / 3 h / 20 °C

5: 98 percent / imidazole / dimethylformamide / 3 h / Ambient temperature

6: 85 percent / MCPBA / CH₂Cl₂ / 1.5 h / 0 °C

7: 1) (CF₃CO)2O, 2) 2,6-lutidine / 1) overnight, RT, 2) 4 h, RT

8: 82 percent / NaBH₄ / methanol / 2 h / Ambient temperature

9: 90 percent / NaIO₄ / RuCl * H₂O / CCl₄; acetonitrile / 2 h / Ambient temperature

With 1H-imidazole; 2,6-dimethylpyridine; sodium tetrahydroborate; sodium periodate; iodine; sodium hydride; sodium hydrogencarbonate; triethylamine; 3-chloro-benzenecarboperoxoic acid; trifluoroacetic anhydride; RuCl * H₂O; In tetrahydrofuran; methanol; tetrachloromethane; dichloromethane; water; N,N-dimethyl-formamide; acetone; acetonitrile;

DOI:10.1055/s-1991-26401

upstream raw materials:

{1-[(S)-5-(tert-Butyl-diphenyl-silanyloxymethyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-2-hydroxy-ethyl}-carbamic acid benzyl ester

2-[(R)-5-(Bis-ethylsulfanyl-methyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-aziridine

2-[(R)-5-(Bis-ethylsulfanyl-methyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-aziridine-1-carboxylic acid benzyl ester

[1-((S)-5-Hydroxymethyl-2,2-dimethyl-[1,3]dioxolan-4-yl)-2-phenylsulfanyl-ethyl]-carbamic acid benzyl ester

Downstream raw materials:

2-amino-5-O-tert-butyldiphenylsilyl-2-deoxy-3,4-O-(1-methylethylidene)-L-xylonic acid

Amino-[(S)-5-(tert-butyl-diphenyl-silanyloxymethyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-acetic acid

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