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

Base Information

Chemical Name:(4R,5R,6R)-5-benzyloxy-4-[1-hydroxy-prop-2-(R)-yl]-2,2,6-trimethyl-1,3-dioxane
CAS No.:862509-84-0
Molecular Formula:C₁₇H₂₆O₄
Molecular Weight:294.391
Hs Code.:

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

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

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

There total 6 articles about (4R,5R,6R)-5-benzyloxy-4-[1-hydroxy-prop-2-(R)-yl]-2,2,6-trimethyl-1,3-dioxane 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: 19.0%

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

: 862509-84-0
(4R,5R,6R)-5-benzyloxy-4-[1-hydroxy-prop-2-(R)-yl]-2,2,6-trimethyl-1,3-dioxane

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

Guidance literature:: With 2,3-dicyano-5,6-dichloro-p-benzoquinone; In dichloromethane; at 0 ℃; for 1.5h; pH=7;
DOI:10.1039/b504149j

Reference yield:

: (R)-1-Benzyloxy-4-(4-methoxy-benzyloxy)-3-methyl-butan-2-one

: 862509-84-0
(4R,5R,6R)-5-benzyloxy-4-[1-hydroxy-prop-2-(R)-yl]-2,2,6-trimethyl-1,3-dioxane

Guidance literature:: Multi-step reaction with 4 steps

1.1: cHex₂BCl; Et₃N / diethyl ether / 2 h / -78 °C

1.2: 16 h / -78 - -20 °C

1.3: 93 percent / H₂O₂ / methanol; H₂O / 3 h / 0 - 20 °C / pH 7

2.1: Me₄NBH(OAc)3 / acetonitrile; acetic acid / 60 h / 4 °C

3.1: PPTS / CH₂Cl₂ / 16 h / 20 °C

4.1: DDQ / CH₂Cl₂ / 1.5 h / 0 °C / pH 7

With dicyclohexylboron chloride; pyridinium p-toluenesulfonate; triethylamine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; tetramethylammonium triacetoxyborohydride; In diethyl ether; dichloromethane; acetic acid; acetonitrile;
DOI:10.1002/1521-3773(20011105)40:21<4055::AID-ANIE4055>3.0.CO;2-H

Reference yield:

: 194934-55-9
(2R,4R,5R)-4-benzyloxy-5-hydroxy-1-(p-methoxybenzyloxy)-2-methyl-3-hexanone

: 862509-84-0
(4R,5R,6R)-5-benzyloxy-4-[1-hydroxy-prop-2-(R)-yl]-2,2,6-trimethyl-1,3-dioxane

Guidance literature:: Multi-step reaction with 3 steps

1: Me₄NBH(OAc)3 / acetonitrile; acetic acid / 60 h / 4 °C

2: PPTS / CH₂Cl₂ / 16 h / 20 °C

3: DDQ / CH₂Cl₂ / 1.5 h / 0 °C / pH 7

With pyridinium p-toluenesulfonate; 2,3-dicyano-5,6-dichloro-p-benzoquinone; tetramethylammonium triacetoxyborohydride; In dichloromethane; acetic acid; acetonitrile;
DOI:10.1002/1521-3773(20011105)40:21<4055::AID-ANIE4055>3.0.CO;2-H