(3S,4R,5Z)-6-bromo-4-(4-methoxybenzyloxy)-3,5-dimethylhex-5-ene-1,2-diol

Base Information

Chemical Name:(3S,4R,5Z)-6-bromo-4-(4-methoxybenzyloxy)-3,5-dimethylhex-5-ene-1,2-diol
CAS No.:1270942-78-3
Molecular Formula:C₁₆H₂₃BrO₄
Molecular Weight:359.26
Hs Code.:

Synonyms:(3S,4R,5Z)-6-bromo-4-(4-methoxybenzyloxy)-3,5-dimethylhex-5-ene-1,2-diol

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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 (3S,4R,5Z)-6-bromo-4-(4-methoxybenzyloxy)-3,5-dimethylhex-5-ene-1,2-diol

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Technology Process of (3S,4R,5Z)-6-bromo-4-(4-methoxybenzyloxy)-3,5-dimethylhex-5-ene-1,2-diol

There total 2 articles about (3S,4R,5Z)-6-bromo-4-(4-methoxybenzyloxy)-3,5-dimethylhex-5-ene-1,2-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: 97.0%

: 1270942-77-2
(Z,3R,4S)-1-bromo-3-(4-methoxybenzyloxy)-2,4-dimethylhexa-1,5-diene

: 1270942-78-3
(3S,4R,5Z)-6-bromo-4-(4-methoxybenzyloxy)-3,5-dimethylhex-5-ene-1,2-diol

Guidance literature:: With osmium(VIII) oxide; water; 4-methylmorpholine N-oxide; In dichloromethane; at 25 ℃; for 4h; optical yield given as %de;
DOI:10.1021/ol200160p

Reference yield:

: 824-94-2
p-methoxybenzyl chloride

: 1270942-78-3
(3S,4R,5Z)-6-bromo-4-(4-methoxybenzyloxy)-3,5-dimethylhex-5-ene-1,2-diol

Guidance literature:: Multi-step reaction with 2 steps

1.1: C₄₉H₃₅IrN₂O₈P₂; water; sodium carbonate / tetrahydrofuran / 144 h / 70 °C / Inert atmosphere; Sealed tube

1.2: 3 h / 0 °C / Inert atmosphere

2.1: osmium(VIII) oxide; water; 4-methylmorpholine N-oxide / dichloromethane / 4 h / 25 °C

With osmium(VIII) oxide; C₄₉H₃₅IrN₂O₈P₂; water; sodium carbonate; 4-methylmorpholine N-oxide; In tetrahydrofuran; dichloromethane; 1.2: Mitsunobu reaction;
DOI:10.1021/ol200160p