(2R,4aR,6S,7R,8R,8aS)-7-Azido-2-phenyl-6-p-tolylsulfanyl-hexahydro-pyrano[3,2-d][1,3]dioxin-8-ol

Base Information

Chemical Name:(2R,4aR,6S,7R,8R,8aS)-7-Azido-2-phenyl-6-p-tolylsulfanyl-hexahydro-pyrano[3,2-d][1,3]dioxin-8-ol
CAS No.:501088-50-2
Molecular Formula:C₂₀H₂₁N₃O₄S
Molecular Weight:399.47
Hs Code.:

Synonyms:(2R,4aR,6S,7R,8R,8aS)-7-Azido-2-phenyl-6-p-tolylsulfanyl-hexahydro-pyrano[3,2-d][1,3]dioxin-8-ol

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Chemical Property of (2R,4aR,6S,7R,8R,8aS)-7-Azido-2-phenyl-6-p-tolylsulfanyl-hexahydro-pyrano[3,2-d][1,3]dioxin-8-ol

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Technology Process of (2R,4aR,6S,7R,8R,8aS)-7-Azido-2-phenyl-6-p-tolylsulfanyl-hexahydro-pyrano[3,2-d][1,3]dioxin-8-ol

There total 6 articles about (2R,4aR,6S,7R,8R,8aS)-7-Azido-2-phenyl-6-p-tolylsulfanyl-hexahydro-pyrano[3,2-d][1,3]dioxin-8-ol 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: 99.0%

: 1125-88-8
benzaldehyde dimethyl acetal

: 501088-37-5
4’-methyl phenyl 2-azido-2-deoxy-1-thio-β-D-glucopyranoside

: 501088-50-2
(2R,4aR,6S,7R,8R,8aS)-7-Azido-2-phenyl-6-p-tolylsulfanyl-hexahydro-pyrano[3,2-d][1,3]dioxin-8-ol

Guidance literature:: With sodium hydrogen sulfate; silica gel; In acetonitrile; at 20 ℃; for 4h;
DOI:10.1055/s-2007-984903

Reference yield:

: 220645-20-5
p-methylphenyl 3,4,6-tri-O-acetyl-2-deoxy-1-thio-2-(2,2,2-trichloroethyloxycarbonylamino)-β-D-glucopyranoside

: 501088-50-2
(2R,4aR,6S,7R,8R,8aS)-7-Azido-2-phenyl-6-p-tolylsulfanyl-hexahydro-pyrano[3,2-d][1,3]dioxin-8-ol

Guidance literature:: Multi-step reaction with 4 steps

1: zinc; AcOH / methanol; CH₂Cl₂ / 1 h / 20 °C

2: NaOMe; MeOH / CH₂Cl₂ / 2 h / 20 °C

3: K₂CO₃; ZnCl₂; triflyl azide / CH₂Cl₂; methanol; H₂O / 18 h / 20 °C

4: 0.41 g / (+/-)-10-camphorsulfonic acid / acetonitrile / 12 h / 20 °C

With methanol; triflic azide; camphor-10-sulfonic acid; sodium methylate; potassium carbonate; acetic acid; zinc(II) chloride; zinc; In methanol; dichloromethane; water; acetonitrile; 2: Zemplen deacetylation;
DOI:10.1021/jo0206420

Reference yield:

: p-methylphenyl 2-amino-2-deoxy-1-thio-β-D-glucopyranoside

: 501088-50-2
(2R,4aR,6S,7R,8R,8aS)-7-Azido-2-phenyl-6-p-tolylsulfanyl-hexahydro-pyrano[3,2-d][1,3]dioxin-8-ol

Guidance literature:: Multi-step reaction with 2 steps

1: K₂CO₃; ZnCl₂; triflyl azide / CH₂Cl₂; methanol; H₂O / 18 h / 20 °C

2: 0.41 g / (+/-)-10-camphorsulfonic acid / acetonitrile / 12 h / 20 °C

With triflic azide; camphor-10-sulfonic acid; potassium carbonate; zinc(II) chloride; In methanol; dichloromethane; water; acetonitrile;
DOI:10.1021/jo0206420