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

Base Information

Chemical Name:4-benzyloxycarbonylamino-1-O-tert-butyldiphenylsilyl-2,3-O-(1-methylethylidene)-4,5-dideoxy-5-phenylthio-D-xylitol
CAS No.:126448-10-0
Molecular Formula:C₃₈H₄₅NO₅SSi
Molecular Weight:655.93
Hs Code.:

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

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

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

There total 13 articles about 4-benzyloxycarbonylamino-1-O-tert-butyldiphenylsilyl-2,3-O-(1-methylethylidene)-4,5-dideoxy-5-phenylthio-D-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: 98.0%

: 126448-17-7
4-benzyloxycarbonylamino-4,5-dideoxy-2,3-O-(1-methylethylidene)-5-phenylthio-D-xylitol

: 58479-61-1
tert-butylchlorodiphenylsilane

: 126448-10-0
4-benzyloxycarbonylamino-1-O-tert-butyldiphenylsilyl-2,3-O-(1-methylethylidene)-4,5-dideoxy-5-phenylthio-D-xylitol

Guidance literature:: With 1H-imidazole; In N,N-dimethyl-formamide; for 3h; Ambient temperature;
DOI:10.1055/s-1991-26401

Reference yield:

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

: 126448-10-0
4-benzyloxycarbonylamino-1-O-tert-butyldiphenylsilyl-2,3-O-(1-methylethylidene)-4,5-dideoxy-5-phenylthio-D-xylitol

Guidance literature:: Multi-step reaction with 7 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

With pyridine; 1H-imidazole; sodium tetrahydroborate; sodium azide; iodine; sodium hydride; sodium hydrogencarbonate; triethylamine; p-toluenesulfonyl chloride; triphenylphosphine; In tetrahydrofuran; 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

: 126448-10-0
4-benzyloxycarbonylamino-1-O-tert-butyldiphenylsilyl-2,3-O-(1-methylethylidene)-4,5-dideoxy-5-phenylthio-D-xylitol

Guidance literature:: Multi-step reaction with 5 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

With 1H-imidazole; sodium tetrahydroborate; iodine; sodium hydride; sodium hydrogencarbonate; triethylamine; In tetrahydrofuran; methanol; dichloromethane; water; N,N-dimethyl-formamide; acetone;
DOI:10.1055/s-1991-26401