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

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Chemical Name:4-benzyloxycarbonylamino-4,5-dideoxy-2,3-O-(1-methylethylidene)-5-phenylthio-D-xylitol
CAS No.:126448-17-7
Molecular Formula:C₂₂H₂₇NO₅S
Molecular Weight:417.526
Hs Code.:

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

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

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

There total 11 articles about 4-benzyloxycarbonylamino-4,5-dideoxy-2,3-O-(1-methylethylidene)-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:

: 126448-16-6
[1-((R)-5-Formyl-2,2-dimethyl-[1,3]dioxolan-4-yl)-2-phenylsulfanyl-ethyl]-carbamic acid benzyl ester

: 126448-17-7
[1-((S)-5-Hydroxymethyl-2,2-dimethyl-[1,3]dioxolan-4-yl)-2-phenylsulfanyl-ethyl]-carbamic acid benzyl ester

Guidance literature:: With sodium tetrahydroborate; In methanol; at 0 ℃; for 3h;
DOI:10.1016/S0040-4039(01)80736-X

Reference yield:

: 126448-16-6
[(S)-1-((4S,5R)-5-Formyl-2,2-dimethyl-[1,3]dioxolan-4-yl)-2-phenylsulfanyl-ethyl]-carbamic acid benzyl ester

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

Guidance literature:: With sodium tetrahydroborate; In methanol; at 20 ℃; for 3h; Yield given;
DOI:10.1055/s-1991-26401

Reference yield:

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

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

Guidance literature:: Multi-step reaction with 6 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

With pyridine; sodium tetrahydroborate; sodium azide; iodine; sodium hydride; sodium hydrogencarbonate; triethylamine; p-toluenesulfonyl chloride; triphenylphosphine; In tetrahydrofuran; methanol; dichloromethane; water; acetone; toluene;
DOI:10.1055/s-1991-26401