(2R,3S,10S)-2-benzyloxy-10-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]undec-5-yn-3-ol

Base Information

Chemical Name:(2R,3S,10S)-2-benzyloxy-10-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]undec-5-yn-3-ol
CAS No.:479484-93-0
Molecular Formula:C₂₃H₃₄O₄
Molecular Weight:374.521
Hs Code.:

Synonyms:(2R,3S,10S)-2-benzyloxy-10-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]undec-5-yn-3-ol

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Chemical Property of (2R,3S,10S)-2-benzyloxy-10-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]undec-5-yn-3-ol

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Technology Process of (2R,3S,10S)-2-benzyloxy-10-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]undec-5-yn-3-ol

There total 8 articles about (2R,3S,10S)-2-benzyloxy-10-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]undec-5-yn-3-ol 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: 89.6%

: 202122-39-2
(R)-2,2-Dimethyl-4-((S)-1-methyl-hex-5-ynyl)-[1,3]dioxolane

: 327186-71-0
(1R)-1-[(2S)-oxiran-2-yl]-1-(benzyloxy)ethane

: 479484-93-0
(2R,3S,10S)-2-benzyloxy-10-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]undec-5-yn-3-ol

Guidance literature:: (R)-2,2-Dimethyl-4-((S)-1-methyl-hex-5-ynyl)-[1,3]dioxolane; With n-butyllithium; In tetrahydrofuran; cyclohexane; at -78 - -40 ℃; for 0.916667h;

(1R)-1-[(2S)-oxiran-2-yl]-1-(benzyloxy)ethane; With boron trifluoride diethyl etherate; In tetrahydrofuran; cyclohexane; at -78 ℃; for 0.5h;
DOI:10.1002/1521-3765(20020816)8:16<3717::AID-CHEM3717>3.0.CO;2-G

Reference yield:

: 76985-26-7
(2S,3R)-3,7-dimethyl-2,3-epoxy-6-octen-1-ol

: 479484-93-0
(2R,3S,10S)-2-benzyloxy-10-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]undec-5-yn-3-ol

Guidance literature:: Multi-step reaction with 7 steps

1.1: NaBH₃CN; BF₃*Et₂O / tetrahydrofuran / 6 h / 20 °C

2.1: H₂SO₄ / acetone / 0.5 h / 0 °C

3.1: O₃ / CH₂Cl₂ / 2 h / -78 °C

3.2: 90 percent / LiAlH₄ / diethyl ether / 1 h / 0 °C

4.1: pyridine / 6 h / -10 - 20 °C

5.1: LiBr; K₂CO₃ / acetone / 0.75 h / Heating

6.1: 95.4 percent / Na; NH₃ / 2 h / -40 °C

7.1: n-BuLi / tetrahydrofuran; cyclohexane / 0.92 h / -78 - -40 °C

7.2: 89.6 percent / BF₃*Et₂O / tetrahydrofuran; cyclohexane / 0.5 h / -78 °C

With pyridine; n-butyllithium; sulfuric acid; boron trifluoride diethyl etherate; ammonia; sodium; sodium cyanoborohydride; potassium carbonate; ozone; lithium bromide; In tetrahydrofuran; dichloromethane; cyclohexane; acetone;
DOI:10.1002/1521-3765(20020816)8:16<3717::AID-CHEM3717>3.0.CO;2-G

Reference yield:

: 156633-81-7
(2R,3S)-3,7-dimethyl-6-octene-1,2-diol

: 479484-93-0
(2R,3S,10S)-2-benzyloxy-10-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]undec-5-yn-3-ol

Guidance literature:: Multi-step reaction with 6 steps

1.1: H₂SO₄ / acetone / 0.5 h / 0 °C

2.1: O₃ / CH₂Cl₂ / 2 h / -78 °C

2.2: 90 percent / LiAlH₄ / diethyl ether / 1 h / 0 °C

3.1: pyridine / 6 h / -10 - 20 °C

4.1: LiBr; K₂CO₃ / acetone / 0.75 h / Heating

5.1: 95.4 percent / Na; NH₃ / 2 h / -40 °C

6.1: n-BuLi / tetrahydrofuran; cyclohexane / 0.92 h / -78 - -40 °C

6.2: 89.6 percent / BF₃*Et₂O / tetrahydrofuran; cyclohexane / 0.5 h / -78 °C

With pyridine; n-butyllithium; sulfuric acid; ammonia; sodium; potassium carbonate; ozone; lithium bromide; In tetrahydrofuran; dichloromethane; cyclohexane; acetone;
DOI:10.1002/1521-3765(20020816)8:16<3717::AID-CHEM3717>3.0.CO;2-G