(2R,3R,4R,5R,6R)-3-(4-methoxybenzyloxy)-4-(1,3-dioxolan-2-yl)-4,5-dimethyloct-1,2,5,6-tetraol

Base Information

Chemical Name:(2R,3R,4R,5R,6R)-3-(4-methoxybenzyloxy)-4-(1,3-dioxolan-2-yl)-4,5-dimethyloct-1,2,5,6-tetraol
CAS No.:536737-78-7
Molecular Formula:C₂₁H₃₄O₈
Molecular Weight:414.496
Hs Code.:

Synonyms:(2R,3R,4R,5R,6R)-3-(4-methoxybenzyloxy)-4-(1,3-dioxolan-2-yl)-4,5-dimethyloct-1,2,5,6-tetraol

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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 (2R,3R,4R,5R,6R)-3-(4-methoxybenzyloxy)-4-(1,3-dioxolan-2-yl)-4,5-dimethyloct-1,2,5,6-tetraol

Chemical Property:

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Technology Process of (2R,3R,4R,5R,6R)-3-(4-methoxybenzyloxy)-4-(1,3-dioxolan-2-yl)-4,5-dimethyloct-1,2,5,6-tetraol

There total 5 articles about (2R,3R,4R,5R,6R)-3-(4-methoxybenzyloxy)-4-(1,3-dioxolan-2-yl)-4,5-dimethyloct-1,2,5,6-tetraol 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: 74.0%

: 536737-77-6
(2R,3R,4S)-3-(4-methoxybenzyloxy)-4-(1,3-dioxolan-2-yl)-4,5-dimethyloct-5(E)-en-1,2-diol

: 536737-78-7
(2R,3R,4R,5R,6R)-3-(4-methoxybenzyloxy)-4-(1,3-dioxolan-2-yl)-4,5-dimethyloct-1,2,5,6-tetraol

Guidance literature:: With osmium(VIII) oxide; potassium carbonate; 1,4-bis(9-O-dihydroquinidine)phthalazine; methanesulfonamide; potassium hexacyanoferrate(III); In water; tert-butyl alcohol; at 4 ℃;
DOI:10.1021/ja034332q

Reference yield:

: 536737-77-6
(2R,3R,4S)-3-(4-methoxybenzyloxy)-4-(1,3-dioxolan-2-yl)-4,5-dimethyloct-5(E)-en-1,2-diol

: (2R,3R,4R,5S,6S)-4-[1,3]Dioxolan-2-yl-3-(4-methoxy-benzyloxy)-4,5-dimethyl-octane-1,2,5,6-tetraol

: 536737-78-7
(2R,3R,4R,5R,6R)-3-(4-methoxybenzyloxy)-4-(1,3-dioxolan-2-yl)-4,5-dimethyloct-1,2,5,6-tetraol

Guidance literature:: With osmium(VIII) oxide; potassium carbonate; 1,4-bis(9-O-dihydroquinidine)phthalazine; methanesulfonamide; potassium hexacyanoferrate(III); In tert-butyl alcohol; at 4 ℃; Title compound not separated from byproducts;
DOI:10.1021/ja034332q

Reference yield:

: 824-94-2
p-methoxybenzyl chloride

: 536737-78-7
(2R,3R,4R,5R,6R)-3-(4-methoxybenzyloxy)-4-(1,3-dioxolan-2-yl)-4,5-dimethyloct-1,2,5,6-tetraol

Guidance literature:: Multi-step reaction with 3 steps

1.1: KH / tetrahydrofuran / 1 h / 20 °C

1.2: 80 percent / tetrahydrofuran / 20 °C

2.1: 95 percent / tetrabutylammonium fluoride / tetrahydrofuran / 3 h / 20 °C

3.1: (DHQD)2-PHAL; OsO₄; aq. K₂CO₃ / K₃[Fe(CN)6]; methanesulfonamide / 2-methyl-propan-2-ol / 4 °C

With osmium(VIII) oxide; tetrabutyl ammonium fluoride; potassium hydride; potassium carbonate; 1,4-bis(9-O-dihydroquinidine)phthalazine; methanesulfonamide; potassium hexacyanoferrate(III); In tetrahydrofuran; tert-butyl alcohol; 3.1: Sharpless asymmetric dihydroxylation;
DOI:10.1021/ja034332q