(4R,5R)-2-((Z)-Hex-1-enyl)-4,5-bis-(methoxy-diphenyl-methyl)-[1,3,2]dioxaborolane

Base Information

Chemical Name:(4R,5R)-2-((Z)-Hex-1-enyl)-4,5-bis-(methoxy-diphenyl-methyl)-[1,3,2]dioxaborolane
CAS No.:296241-77-5
Molecular Formula:C₃₆H₃₉BO₄
Molecular Weight:546.514
Hs Code.:

Synonyms:(4R,5R)-2-((Z)-Hex-1-enyl)-4,5-bis-(methoxy-diphenyl-methyl)-[1,3,2]dioxaborolane

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Chemical Property of (4R,5R)-2-((Z)-Hex-1-enyl)-4,5-bis-(methoxy-diphenyl-methyl)-[1,3,2]dioxaborolane

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Technology Process of (4R,5R)-2-((Z)-Hex-1-enyl)-4,5-bis-(methoxy-diphenyl-methyl)-[1,3,2]dioxaborolane

There total 3 articles about (4R,5R)-2-((Z)-Hex-1-enyl)-4,5-bis-(methoxy-diphenyl-methyl)-[1,3,2]dioxaborolane 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: 68.0%

: 16538-47-9
(Z)-1-iodohex-1-ene

: 130874-89-4
(2R,3R)-1,4-dimethoxy-1,1,4,4-tetraphenyl-2,3-butandiol

: 296241-77-5
(4R,5R)-2-((Z)-Hex-1-enyl)-4,5-bis-(methoxy-diphenyl-methyl)-[1,3,2]dioxaborolane

Guidance literature:: (Z)-1-iodohex-1-ene; With tert.-butyl lithium; In diethyl ether; at -78 ℃; for 2h;

With Triisopropyl borate; In diethyl ether; at -78 - 20 ℃;

(2R,3R)-1,4-dimethoxy-1,1,4,4-tetraphenyl-2,3-butandiol; In diethyl ether; at 20 ℃; for 18h; Further stages.;
DOI:10.1002/1099-0690(200007)2000:14<2557::aid-ejoc2557>3.0.co;2-i

Reference yield:

: 1119-67-1
1-iodo-1-hexyne

: 296241-77-5
(4R,5R)-2-((Z)-Hex-1-enyl)-4,5-bis-(methoxy-diphenyl-methyl)-[1,3,2]dioxaborolane

Guidance literature:: Multi-step reaction with 2 steps

1.1: dipotassium azodicarboxylate / methanol; pyridine / 0 °C

2.1: tBuLi / diethyl ether / 2 h / -78 °C

2.2: B(OiPr)3 / diethyl ether / -78 - 20 °C

2.3: 68 percent / diethyl ether / 18 h / 20 °C

With tert.-butyl lithium; potassium diazodicarboxylate; In pyridine; methanol; diethyl ether; 1.1: Reduction / 2.1: Metallation / 2.2: hydroboration / 2.3: Esterification;
DOI:10.1002/1099-0690(200007)2000:14<2557::aid-ejoc2557>3.0.co;2-i

Reference yield:

: 693-02-7
hex-1-yne

: 296241-77-5
(4R,5R)-2-((Z)-Hex-1-enyl)-4,5-bis-(methoxy-diphenyl-methyl)-[1,3,2]dioxaborolane

Guidance literature:: Multi-step reaction with 3 steps

1.1: n-BuLi / tetrahydrofuran / -78 - 20 °C

1.2: 78 percent / I₂ / tetrahydrofuran / -78 - 20 °C

2.1: dipotassium azodicarboxylate / methanol; pyridine / 0 °C

3.1: tBuLi / diethyl ether / 2 h / -78 °C

3.2: B(OiPr)3 / diethyl ether / -78 - 20 °C

3.3: 68 percent / diethyl ether / 18 h / 20 °C

With n-butyllithium; tert.-butyl lithium; potassium diazodicarboxylate; In tetrahydrofuran; pyridine; methanol; diethyl ether; 1.1: Metallation / 1.2: Iodination / 2.1: Reduction / 3.1: Metallation / 3.2: hydroboration / 3.3: Esterification;
DOI:10.1002/1099-0690(200007)2000:14<2557::aid-ejoc2557>3.0.co;2-i