(4aR,6S,7R,8R,8aR)-6-((2R,3S,4R,5R,6S)-4,5-Dihydroxy-2-hydroxymethyl-6-phenylsulfanyl-tetrahydro-pyran-3-yloxy)-2,2-dimethyl-hexahydro-pyrano[3,2-d][1,3]dioxine-7,8-diol

Base Information

Chemical Name:(4aR,6S,7R,8R,8aR)-6-((2R,3S,4R,5R,6S)-4,5-Dihydroxy-2-hydroxymethyl-6-phenylsulfanyl-tetrahydro-pyran-3-yloxy)-2,2-dimethyl-hexahydro-pyrano[3,2-d][1,3]dioxine-7,8-diol
CAS No.:117606-38-9
Molecular Formula:C₂₁H₃₀O₁₀S
Molecular Weight:474.529
Hs Code.:

(4aR,6S,7R,8R,8aR)-6-((2R,3S,4R,5R,6S)-4,5-Dihydroxy-2-hydroxymethyl-6-phenylsulfanyl-tetrahydro-pyran-3-yloxy)-2,2-dimethyl-hexahydro-pyrano[3,2-d][1,3]dioxine-7,8-diol

Synonyms:(4aR,6S,7R,8R,8aR)-6-((2R,3S,4R,5R,6S)-4,5-Dihydroxy-2-hydroxymethyl-6-phenylsulfanyl-tetrahydro-pyran-3-yloxy)-2,2-dimethyl-hexahydro-pyrano[3,2-d][1,3]dioxine-7,8-diol

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Chemical Property of (4aR,6S,7R,8R,8aR)-6-((2R,3S,4R,5R,6S)-4,5-Dihydroxy-2-hydroxymethyl-6-phenylsulfanyl-tetrahydro-pyran-3-yloxy)-2,2-dimethyl-hexahydro-pyrano[3,2-d][1,3]dioxine-7,8-diol

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Technology Process of (4aR,6S,7R,8R,8aR)-6-((2R,3S,4R,5R,6S)-4,5-Dihydroxy-2-hydroxymethyl-6-phenylsulfanyl-tetrahydro-pyran-3-yloxy)-2,2-dimethyl-hexahydro-pyrano[3,2-d][1,3]dioxine-7,8-diol

There total 1 articles about (4aR,6S,7R,8R,8aR)-6-((2R,3S,4R,5R,6S)-4,5-Dihydroxy-2-hydroxymethyl-6-phenylsulfanyl-tetrahydro-pyran-3-yloxy)-2,2-dimethyl-hexahydro-pyrano[3,2-d][1,3]dioxine-7,8-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:

: 27891-73-2,27894-87-7,5329-58-8
β-phenylsulfanyl lactoside

: 77-76-9
2,2-dimethoxy-propane

: 117606-38-9
(4aR,6S,7R,8R,8aR)-6-((2R,3S,4R,5R,6S)-4,5-Dihydroxy-2-hydroxymethyl-6-phenylsulfanyl-tetrahydro-pyran-3-yloxy)-2,2-dimethyl-hexahydro-pyrano[3,2-d][1,3]dioxine-7,8-diol

Guidance literature:: toluene-4-sulfonic acid; In N,N-dimethyl-formamide; at 25 ℃; for 2h;
DOI:10.1016/0008-6215(90)84079-A

Reference yield:

: 3282-30-2
pivaloyl chloride

: 117606-38-9
(4aR,6S,7R,8R,8aR)-6-((2R,3S,4R,5R,6S)-4,5-Dihydroxy-2-hydroxymethyl-6-phenylsulfanyl-tetrahydro-pyran-3-yloxy)-2,2-dimethyl-hexahydro-pyrano[3,2-d][1,3]dioxine-7,8-diol

: 117606-39-0
phenyl O-(4,6-di-O-isopropylidene-2,3-di-O-pivaloyl-β-D-galactopyranosyl)-(1->4)-2,3,6-tri-O-pivaloyl-1-thio-β-D-glucopyranoside

Guidance literature:: dmap; In pyridine; at 75 ℃; for 40h; Yield given;
DOI:10.1016/0008-6215(90)84079-A

Reference yield:

: 117606-38-9
(4aR,6S,7R,8R,8aR)-6-((2R,3S,4R,5R,6S)-4,5-Dihydroxy-2-hydroxymethyl-6-phenylsulfanyl-tetrahydro-pyran-3-yloxy)-2,2-dimethyl-hexahydro-pyrano[3,2-d][1,3]dioxine-7,8-diol

: 117606-41-4
phenyl O-(6-O-benzoyl-2,3-di-O-pivaloyl-β-D-galactopyranosyl)-(1->4)-2,3,6-tri-O-pivaloyl-1-thio-β-D-glucopyranoside

Guidance literature:: Multi-step reaction with 3 steps

1: DMAP / pyridine / 40 h / 75 °C

2: 95 percent / CF₃COOH / tetrahydrofuran; H₂O / 1.5 h / 0 °C

3: 80 percent / Et₃N / dimethylformamide / 0.5 h / -20 - -10 °C

With dmap; triethylamine; trifluoroacetic acid; In tetrahydrofuran; pyridine; water; N,N-dimethyl-formamide;
DOI:10.1021/ja00231a071