phenyl 4-O-acetyl-2,6-di-O-benzyl-3-deoxy-1-thio-β-D-xylo-hexopyranoside

Base Information

Chemical Name:phenyl 4-O-acetyl-2,6-di-O-benzyl-3-deoxy-1-thio-β-D-xylo-hexopyranoside
CAS No.:478687-06-8
Molecular Formula:C₂₈H₃₀O₅S
Molecular Weight:478.609
Hs Code.:

Synonyms:phenyl 4-O-acetyl-2,6-di-O-benzyl-3-deoxy-1-thio-β-D-xylo-hexopyranoside

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Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

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Chemical Property of phenyl 4-O-acetyl-2,6-di-O-benzyl-3-deoxy-1-thio-β-D-xylo-hexopyranoside

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Technology Process of phenyl 4-O-acetyl-2,6-di-O-benzyl-3-deoxy-1-thio-β-D-xylo-hexopyranoside

There total 5 articles about phenyl 4-O-acetyl-2,6-di-O-benzyl-3-deoxy-1-thio-β-D-xylo-hexopyranoside 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:

: Acetic acid (2R,3S,4S,5R,6S)-5-benzyloxy-2-benzyloxymethyl-4-phenoxythiocarbonyloxy-6-phenylsulfanyl-tetrahydro-pyran-3-yl ester

: 478687-06-8
phenyl 4-O-acetyl-2,6-di-O-benzyl-3-deoxy-1-thio-β-D-xylo-hexopyranoside

Guidance literature:: With 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride; In benzene; at 80 ℃; for 2h;
DOI:10.1016/S0008-6215(02)00159-3

Reference yield:

: 100-39-0
benzyl bromide

: 478687-06-8
phenyl 4-O-acetyl-2,6-di-O-benzyl-3-deoxy-1-thio-β-D-xylo-hexopyranoside

Guidance literature:: Multi-step reaction with 5 steps

1.1: 86 percent / NaH / dimethylformamide / 0 - 20 °C

2.1: 91 percent / AcOH / H₂O / 4 h / 80 °C

3.1: TsOH*H₂O / benzene

3.2: 87.2 percent / AcOH / H₂O / 0.33 h / 20 °C

4.1: 4-(dimethylamino)-pyridine / CH₂Cl₂ / 0 - 20 °C

5.1: 0.74 g / Bu₃SnH; AIBN / benzene / 2 h / 80 °C

With dmap; 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride; sodium hydride; toluene-4-sulfonic acid; acetic acid; In dichloromethane; water; N,N-dimethyl-formamide; benzene; 5.1: Barton-McCombie deoxygenation;
DOI:10.1016/S0008-6215(02)00159-3

Reference yield:

: 124476-96-6
phenyl 2,6-di-O-benzyl-3,4-O-isopropylidene-1-thio-β-D-galactopyranoside

: 478687-06-8
phenyl 4-O-acetyl-2,6-di-O-benzyl-3-deoxy-1-thio-β-D-xylo-hexopyranoside

Guidance literature:: Multi-step reaction with 4 steps

1.1: 91 percent / AcOH / H₂O / 4 h / 80 °C

2.1: TsOH*H₂O / benzene

2.2: 87.2 percent / AcOH / H₂O / 0.33 h / 20 °C

3.1: 4-(dimethylamino)-pyridine / CH₂Cl₂ / 0 - 20 °C

4.1: 0.74 g / Bu₃SnH; AIBN / benzene / 2 h / 80 °C

With dmap; 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride; toluene-4-sulfonic acid; acetic acid; In dichloromethane; water; benzene; 4.1: Barton-McCombie deoxygenation;
DOI:10.1016/S0008-6215(02)00159-3