(2R,4R,5R)-4-benzyloxy-5-hydroxy-1-(p-methoxybenzyloxy)-2-methyl-3-hexanone

Base Information

• Chemical Name: (2R,4R,5R)-4-benzyloxy-5-hydroxy-1-(p-methoxybenzyloxy)-2-methyl-3-hexanone
• CAS No.: 194934-55-9
• Molecular Formula: C₂₂H₂₈O₅
• Molecular Weight: 372.461

Synonyms:(2R,4R,5R)-4-benzyloxy-5-hydroxy-1-(p-methoxybenzyloxy)-2-methyl-3-hexanone

Chemical Property of (2R,4R,5R)-4-benzyloxy-5-hydroxy-1-(p-methoxybenzyloxy)-2-methyl-3-hexanone

Chemical Property:

Purity/Quality:

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Technology Process of (2R,4R,5R)-4-benzyloxy-5-hydroxy-1-(p-methoxybenzyloxy)-2-methyl-3-hexanone

There total 3 articles about (2R,4R,5R)-4-benzyloxy-5-hydroxy-1-(p-methoxybenzyloxy)-2-methyl-3-hexanone 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: 93.0%

acetaldehyde (75-07-0,9002-91-9) + (R)-1-Benzyloxy-4-(4-methoxy-benzyloxy)-3-methyl-butan-2-one → (2R,4R,5R)-4-benzyloxy-5-hydroxy-1-(p-methoxybenzyloxy)-2-methyl-3-hexanone (194934-55-9)

Guidance literature:

(R)-1-Benzyloxy-4-(4-methoxy-benzyloxy)-3-methyl-butan-2-one; With dicyclohexylboron chloride; triethylamine; In diethyl ether; at -78 ℃; for 2h;

acetaldehyde; at -78 - -20 ℃; for 16h;

With dihydrogen peroxide; In methanol; water; at 0 - 20 ℃; for 3h; pH=7;

DOI:10.1002/1521-3773(20011105)40:21<4055::AID-ANIE4055>3.0.CO;2-H

Reference yield:

acetaldehyde (75-07-0,9002-91-9) + C32H45BO4 (194934-54-8) → (2R,4R,5R)-4-benzyloxy-5-hydroxy-1-(p-methoxybenzyloxy)-2-methyl-3-hexanone (194934-55-9)

Guidance literature:

acetaldehyde; C₃₂H₄₅BO₄; In diethyl ether; at -78 - -20 ℃; for 16.5h;

With dihydrogen peroxide; In methanol; at 0 ℃; for 3h; pH=7;

DOI:10.1039/b504149j

Reference yield:

(R)-1-Benzyloxy-4-(4-methoxy-benzyloxy)-3-methyl-butan-2-one → (2R,4R,5R)-4-benzyloxy-5-hydroxy-1-(p-methoxybenzyloxy)-2-methyl-3-hexanone (194934-55-9)

Guidance literature:

Multi-step reaction with 2 steps

1.1: Et₃N / diethyl ether / 2 h / 0 °C

2.1: diethyl ether / 16.5 h / -78 - -20 °C

2.2: 13.9 g / aq. H₂O₂ / methanol; various solvent(s) / 3 h / 0 °C / pH 7

With triethylamine; In diethyl ether;

DOI:10.1039/b504149j

upstream raw materials:

acetaldehyde

C₃₂H₄₅BO₄

Downstream raw materials:

(2R,3R,4R,5R)-3-benzyloxy-6-(p-methoxybenzyloxy)-5-methylhexane-2,4-diol

(4R,5R,6R)-5-benzyloxy-4-[1-hydroxy-prop-2-(R)-yl]-2,2,6-trimethyl-1,3-dioxane

(S)-2-[5-(R)-benzyloxy-2,2,6-(6R)-trimethyl-1,3-dioxan-4-(R)-yl]-propionaldehyde

methyl (2E,4R)-4-[5-(R)-benzyloxy-2,2,6-(6R)-trimethyl-1,3-dioxan-4-(R)-yl]-pent-2-enoate

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