(2R,4aR,6S,8S,8aS)-2-phenyl-6-(prop-2-ynyloxy)hexahydropyrano[3,2-d][1,3]dioxin-8-ol

Base Information

Chemical Name:(2R,4aR,6S,8S,8aS)-2-phenyl-6-(prop-2-ynyloxy)hexahydropyrano[3,2-d][1,3]dioxin-8-ol
CAS No.:940933-61-9
Molecular Formula:C₁₆H₁₈O₅
Molecular Weight:290.316
Hs Code.:

Synonyms:(2R,4aR,6S,8S,8aS)-2-phenyl-6-(prop-2-ynyloxy)hexahydropyrano[3,2-d][1,3]dioxin-8-ol

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Chemical Property of (2R,4aR,6S,8S,8aS)-2-phenyl-6-(prop-2-ynyloxy)hexahydropyrano[3,2-d][1,3]dioxin-8-ol

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Technology Process of (2R,4aR,6S,8S,8aS)-2-phenyl-6-(prop-2-ynyloxy)hexahydropyrano[3,2-d][1,3]dioxin-8-ol

There total 2 articles about (2R,4aR,6S,8S,8aS)-2-phenyl-6-(prop-2-ynyloxy)hexahydropyrano[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: 82.0%

: 940933-60-8
(2R,4aR,6S,8aR)-2-phenyl-6-(prop-2-ynyloxy)tetrahydropyrano[3,2-d][1,3]dioxin-8(8aH)-one

: 940933-61-9
(2R,4aR,6S,8S,8aS)-2-phenyl-6-(prop-2-ynyloxy)hexahydropyrano[3,2-d][1,3]dioxin-8-ol

Guidance literature:: With tert.-butyl lithium; diisobutylaluminium hydride; In tetrahydrofuran; pentane; at -78 ℃; for 1.5h; Inert atmosphere;
DOI:10.1021/jo801503c

Reference yield:

: 940933-59-5
propargyl 2,3:4,6-di-O-benzylidene-D-mannopyranoside

: 940933-61-9
(2R,4aR,6S,8S,8aS)-2-phenyl-6-(prop-2-ynyloxy)hexahydropyrano[3,2-d][1,3]dioxin-8-ol

Guidance literature:: Multi-step reaction with 2 steps

1: 63 percent / n-BuLi / tetrahydrofuran; hexane / 1 h / -40 - -30 °C

2: 63 percent / DIBAL; t-BuLi / tetrahydrofuran; pentane / 1.5 h / -78 °C

With n-butyllithium; tert.-butyl lithium; diisobutylaluminium hydride; In tetrahydrofuran; hexane; pentane;
DOI:10.1021/ja069342g

Reference yield:

: 940933-61-9
(2R,4aR,6S,8S,8aS)-2-phenyl-6-(prop-2-ynyloxy)hexahydropyrano[3,2-d][1,3]dioxin-8-ol

: 940933-72-2
t-butyldimethyl((2R,4aR,6S,8S,8aR)-2-phenyl-6-(propa-1,2-dienyloxy)hexahydropyrano[3,2-d][1,3]dioxin-8-yloxy)silane

Guidance literature:: Multi-step reaction with 2 steps

1: 66 percent / pyridine / CH₂Cl₂ / 0.58 h / 0 °C

2: 73 percent / t-BuOK / tetrahydrofuran / 1 h / 60 °C

With pyridine; potassium tert-butylate; In tetrahydrofuran; dichloromethane;
DOI:10.1021/ja069342g