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

Base Information

• Chemical Name: 4-benzyloxycarbonylamino-4,5-dideoxy-2,3-O-(1-methylethylidene)-5-phenylthio-D-xylose diethyl dithioacetal
• CAS No.: 126448-09-7
• Molecular Formula: C₂₆H₃₅NO₄S₃
• Molecular Weight: 521.766
• Mol file: 126448-09-7.mol

Synonyms:4-benzyloxycarbonylamino-4,5-dideoxy-2,3-O-(1-methylethylidene)-5-phenylthio-D-xylose diethyl dithioacetal

Chemical Property of 4-benzyloxycarbonylamino-4,5-dideoxy-2,3-O-(1-methylethylidene)-5-phenylthio-D-xylose diethyl dithioacetal

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 4-benzyloxycarbonylamino-4,5-dideoxy-2,3-O-(1-methylethylidene)-5-phenylthio-D-xylose diethyl dithioacetal

There total 7 articles about 4-benzyloxycarbonylamino-4,5-dideoxy-2,3-O-(1-methylethylidene)-5-phenylthio-D-xylose diethyl dithioacetal 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: 85.0%

4,5-(benzyloxycarbonyl)imino-4,5-dideoxy-2,3-O-(1-methylethylidene)-D-xylose diethyl dithioacetal (126448-08-6) + thiophenol (108-98-5) → 4-benzyloxycarbonylamino-4,5-dideoxy-2,3-O-(1-methylethylidene)-5-phenylthio-D-xylose diethyl dithioacetal (126448-09-7)

Guidance literature:

With sodium hydride; In tetrahydrofuran; 1) RT, 30 min, 2) RT, 4 h;

DOI:10.1055/s-1991-26401

Reference yield: 75.0%

2-[(R)-5-(Bis-ethylsulfanyl-methyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-aziridine-1-carboxylic acid benzyl ester (126448-08-6) + thiophenol (108-98-5) → {1-[(R)-5-(Bis-ethylsulfanyl-methyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-2-phenylsulfanyl-ethyl}-carbamic acid benzyl ester (126448-09-7)

Guidance literature:

With sodium hydride; In tetrahydrofuran; for 4h; Ambient temperature;

DOI:10.1016/S0040-4039(01)80736-X

Reference yield:

2,3-O-isopropylidene-L-arabinose diethyl mercaptal (53872-72-3) → 4-benzyloxycarbonylamino-4,5-dideoxy-2,3-O-(1-methylethylidene)-5-phenylthio-D-xylose diethyl dithioacetal (126448-09-7)

Guidance literature:

Multi-step reaction with 4 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

With pyridine; sodium azide; sodium hydride; triethylamine; p-toluenesulfonyl chloride; triphenylphosphine; In tetrahydrofuran; dichloromethane; toluene;

DOI:10.1055/s-1991-26401

upstream raw materials:

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

thiophenol

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

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

Downstream raw materials:

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

2-benzyloxycarbonylamino-5-O-tert-butyldiphenylsilyl-2-deoxy-3,4-O-(1-methylethylidene)-L-xylose O-acetyl S-phenyl monothioacetal

4-benzyloxycarbonylamino-1-O-tert-butyldiphenylsilyl-4,5-dideoxy-2,3-O-(1-methylethylidene)-5-phenylsulfinyl-D-xylitol

4-benzyloxycarbonylamino-1-O-tert-butyldiphenylsilyl-2,3-O-(1-methylethylidene)-4,5-dideoxy-5-phenylthio-D-xylitol