(4R,5S)-2-Phenyl-5-((2R,4S,5R)-2-phenyl-4-vinyl-[1,3]dioxan-5-yloxy)-4-vinyl-[1,3,2]dioxaborinane

Base Information

• Chemical Name: (4R,5S)-2-Phenyl-5-((2R,4S,5R)-2-phenyl-4-vinyl-[1,3]dioxan-5-yloxy)-4-vinyl-[1,3,2]dioxaborinane
• CAS No.: 475641-73-7
• Molecular Formula: C₂₃H₂₅BO₅
• Molecular Weight: 392.26

Synonyms:(4R,5S)-2-Phenyl-5-((2R,4S,5R)-2-phenyl-4-vinyl-[1,3]dioxan-5-yloxy)-4-vinyl-[1,3,2]dioxaborinane

Chemical Property of (4R,5S)-2-Phenyl-5-((2R,4S,5R)-2-phenyl-4-vinyl-[1,3]dioxan-5-yloxy)-4-vinyl-[1,3,2]dioxaborinane

Chemical Property:

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Technology Process of (4R,5S)-2-Phenyl-5-((2R,4S,5R)-2-phenyl-4-vinyl-[1,3]dioxan-5-yloxy)-4-vinyl-[1,3,2]dioxaborinane

There total 14 articles about (4R,5S)-2-Phenyl-5-((2R,4S,5R)-2-phenyl-4-vinyl-[1,3]dioxan-5-yloxy)-4-vinyl-[1,3,2]dioxaborinane 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: 46.0%

Methyltriphenylphosphonium bromide (1779-49-3) + (2R,4R,5R)-2-Phenyl-5-((4R,5S)-2-phenyl-4-vinyl-[1,3,2]dioxaborinan-5-yloxy)-[1,3]dioxane-4-carbaldehyde → (4R,5S)-2-Phenyl-5-((2R,4S,5R)-2-phenyl-4-vinyl-[1,3]dioxan-5-yloxy)-4-vinyl-[1,3,2]dioxaborinane (475641-73-7)

Guidance literature:

Methyltriphenylphosphonium bromide; With sodium hexamethyldisilazane; In tetrahydrofuran; at 22 ℃; for 1h;

(2R,4R,5R)-2-Phenyl-5-((4R,5S)-2-phenyl-4-vinyl-[1,3,2]dioxaborinan-5-yloxy)-[1,3]dioxane-4-carbaldehyde; In tetrahydrofuran; at -78 - 22 ℃; for 9h;

DOI:10.1055/s-2002-33527

Reference yield:

((2R,3S,6S)-3-acetoxy-6-cyano-3,6-dihydro-2H-pyran-2-yl)methyl acetate (83938-00-5) → (4R,5S)-2-Phenyl-5-((2R,4S,5R)-2-phenyl-4-vinyl-[1,3]dioxan-5-yloxy)-4-vinyl-[1,3,2]dioxaborinane (475641-73-7)

Guidance literature:

Multi-step reaction with 13 steps

1.1: Amberlyst 15 / methanol / 24 h / Heating

2.1: Amberlyst 15 / CHCl₃ / 22.5 h

3.1: 100 percent / aq. OsO₄; NMO / dioxane / 96 h / 20 °C

4.1: 100 percent / 2,6-lutidine / CH₂Cl₂ / 72 h / 0 - 22 °C

5.1: DIBALH / CH₂Cl₂ / 0.2 h / -78 °C

6.1: aq. HCl / CH₂Cl₂ / 16 h / 22 °C

7.1: t-BuLi / tetrahydrofuran / 0.33 h / -78 °C

7.2: 79 percent / tetrahydrofuran / 1 h / -78 °C

8.1: 100 percent / TBAF / tetrahydrofuran / 22 °C

9.1: aq. NaIO₄ / dioxane / 22 °C

10.1: NaBH₄ / methanol / 0 °C

11.1: 95 percent / benzene / Heating

12.1: TPAP; NMO; 4 Angstroem molecular sieves / CH₂Cl₂ / 0.2 h

13.1: NaHMDS / tetrahydrofuran / 1 h / 22 °C

13.2: 46 percent / tetrahydrofuran / 9 h / -78 - 22 °C

With 2,6-dimethylpyridine; hydrogenchloride; sodium tetrahydroborate; sodium periodate; osmium(VIII) oxide; N-methyl-2-indolinone; Amberlyst 15; tetrapropylammonium perruthennate; 4 A molecular sieve; tetrabutyl ammonium fluoride; tert.-butyl lithium; sodium hexamethyldisilazane; diisobutylaluminium hydride; In tetrahydrofuran; 1,4-dioxane; methanol; dichloromethane; chloroform; benzene; 13.2: Wittig reaction;

DOI:10.1055/s-2002-33527

Reference yield:

2,3-dideoxy-α-D-erythro-hex-2-enopyranosyl cyanide (88180-36-3) → (4R,5S)-2-Phenyl-5-((2R,4S,5R)-2-phenyl-4-vinyl-[1,3]dioxan-5-yloxy)-4-vinyl-[1,3,2]dioxaborinane (475641-73-7)

Guidance literature:

Multi-step reaction with 12 steps

1.1: Amberlyst 15 / CHCl₃ / 22.5 h

2.1: 100 percent / aq. OsO₄; NMO / dioxane / 96 h / 20 °C

3.1: 100 percent / 2,6-lutidine / CH₂Cl₂ / 72 h / 0 - 22 °C

4.1: DIBALH / CH₂Cl₂ / 0.2 h / -78 °C

5.1: aq. HCl / CH₂Cl₂ / 16 h / 22 °C

6.1: t-BuLi / tetrahydrofuran / 0.33 h / -78 °C

6.2: 79 percent / tetrahydrofuran / 1 h / -78 °C

7.1: 100 percent / TBAF / tetrahydrofuran / 22 °C

8.1: aq. NaIO₄ / dioxane / 22 °C

9.1: NaBH₄ / methanol / 0 °C

10.1: 95 percent / benzene / Heating

11.1: TPAP; NMO; 4 Angstroem molecular sieves / CH₂Cl₂ / 0.2 h

12.1: NaHMDS / tetrahydrofuran / 1 h / 22 °C

12.2: 46 percent / tetrahydrofuran / 9 h / -78 - 22 °C

With 2,6-dimethylpyridine; hydrogenchloride; sodium tetrahydroborate; sodium periodate; osmium(VIII) oxide; N-methyl-2-indolinone; Amberlyst 15; tetrapropylammonium perruthennate; 4 A molecular sieve; tetrabutyl ammonium fluoride; tert.-butyl lithium; sodium hexamethyldisilazane; diisobutylaluminium hydride; In tetrahydrofuran; 1,4-dioxane; methanol; dichloromethane; chloroform; benzene; 12.2: Wittig reaction;

DOI:10.1055/s-2002-33527

upstream raw materials:

Methyltriphenylphosphonium bromide

((2R,3S,6S)-3-acetoxy-6-cyano-3,6-dihydro-2H-pyran-2-yl)methyl acetate

2,3-dideoxy-α-D-erythro-hex-2-enopyranosyl cyanide

4,6-O-Benzylidene-2,3-dideoxy-α-D-erythro-hex-2-enopyranosyl cyanide

Downstream raw materials:

(2S,3R)-2-((2R,4S,5R)-2-Phenyl-4-vinyl-[1,3]dioxan-5-yloxy)-pent-4-ene-1,3-diol

2,2-Dimethyl-propionic acid (2R,4aR,6S,7R,9aS)-7-hydroxy-2-phenyl-4a,6,7,9a-tetrahydro-4H-1,3,5-trioxa-benzocyclohepten-6-ylmethyl ester

2,2-Dimethyl-propionic acid (2S,3R)-3-hydroxy-2-((2R,4S,5R)-2-phenyl-4-vinyl-[1,3]dioxan-5-yloxy)-pent-4-enyl ester

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