(2S,3S,4aR,8aS)-2-((2S,3S)-3-Benzyloxy-tetrahydro-pyran-2-yl)-octahydro-pyrano[3,2-b]pyran-2,3-diol

Base Information

Chemical Name:(2S,3S,4aR,8aS)-2-((2S,3S)-3-Benzyloxy-tetrahydro-pyran-2-yl)-octahydro-pyrano[3,2-b]pyran-2,3-diol
CAS No.:183722-23-8
Molecular Formula:C₂₀H₂₈O₆
Molecular Weight:364.439
Hs Code.:

Synonyms:(2S,3S,4aR,8aS)-2-((2S,3S)-3-Benzyloxy-tetrahydro-pyran-2-yl)-octahydro-pyrano[3,2-b]pyran-2,3-diol

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Chemical Property of (2S,3S,4aR,8aS)-2-((2S,3S)-3-Benzyloxy-tetrahydro-pyran-2-yl)-octahydro-pyrano[3,2-b]pyran-2,3-diol

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Technology Process of (2S,3S,4aR,8aS)-2-((2S,3S)-3-Benzyloxy-tetrahydro-pyran-2-yl)-octahydro-pyrano[3,2-b]pyran-2,3-diol

There total 5 articles about (2S,3S,4aR,8aS)-2-((2S,3S)-3-Benzyloxy-tetrahydro-pyran-2-yl)-octahydro-pyrano[3,2-b]pyran-2,3-diol 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%

: 183722-21-6
(4aS,8aR)-6-((2S,3S)-3-Benzyloxy-tetrahydro-pyran-2-yl)-2,3,4,4a,8,8a-hexahydro-pyrano[3,2-b]pyran

: 183902-86-5
(2R,3R,4aR,8aS)-2-((2S,3S)-3-Benzyloxy-tetrahydro-pyran-2-yl)-octahydro-pyrano[3,2-b]pyran-2,3-diol

: 183722-23-8
(2S,3S,4aR,8aS)-2-((2S,3S)-3-Benzyloxy-tetrahydro-pyran-2-yl)-octahydro-pyrano[3,2-b]pyran-2,3-diol

Guidance literature:: With AD-mix-α; methanesulfonamide; In water; tert-butyl alcohol; at 0 ℃; for 36h;
DOI:10.1021/ja962862z

Reference yield:

: 183902-86-5
(2R,3R,4aR,8aS)-2-((2S,3S)-3-Benzyloxy-tetrahydro-pyran-2-yl)-octahydro-pyrano[3,2-b]pyran-2,3-diol

: 183722-23-8
(2S,3S,4aR,8aS)-2-((2S,3S)-3-Benzyloxy-tetrahydro-pyran-2-yl)-octahydro-pyrano[3,2-b]pyran-2,3-diol

Guidance literature:: With potassium carbonate; In tert-butyl alcohol; at 25 ℃;
DOI:10.1021/ja962862z

Reference yield:

: (2S,3S)-3-Benzyloxy-tetrahydro-pyran-2-carboxylic acid

: 183722-23-8
(2S,3S,4aR,8aS)-2-((2S,3S)-3-Benzyloxy-tetrahydro-pyran-2-yl)-octahydro-pyrano[3,2-b]pyran-2,3-diol

Guidance literature:: Multi-step reaction with 4 steps

1: 81 percent / 2-(chloromethyl)pyridinium iodide, Et₃N, 4-DMAP / CH₂Cl₂ / 3 h / 25 °C

2: 50 percent / μ-chloro-μ-methylene-dimethylaluminium / tetrahydrofuran / 1.) 25 deg C, 0.5 h, 2.) reflux, 4 h

3: AD mix α, MeSO2NH2 / 2-methyl-propan-2-ol; H2O / 36 h / 0 °C

4: aq. K₂CO₃ / 2-methyl-propan-2-ol / 25 °C

With dmap; AD-mix-α; Tebbe's reagent; methanesulfonamide; 2-chloromethylpyridinium iodide; potassium carbonate; triethylamine; In tetrahydrofuran; dichloromethane; water; tert-butyl alcohol;
DOI:10.1021/ja962862z