(2R,4S,5R)-4-Allyl-5-[(1S,2R)-2-(tert-butyl-dimethyl-silanyloxy)-1-(tert-butyl-dimethyl-silanyloxymethyl)-pent-4-enyloxy]-2-phenyl-[1,3]dioxane

Base Information

• Chemical Name: (2R,4S,5R)-4-Allyl-5-[(1S,2R)-2-(tert-butyl-dimethyl-silanyloxy)-1-(tert-butyl-dimethyl-silanyloxymethyl)-pent-4-enyloxy]-2-phenyl-[1,3]dioxane
• CAS No.: 475641-89-5
• Molecular Formula: C₃₁H₅₄O₅Si₂
• Molecular Weight: 562.938
• Mol file: 475641-89-5.mol

Synonyms:(2R,4S,5R)-4-Allyl-5-[(1S,2R)-2-(tert-butyl-dimethyl-silanyloxy)-1-(tert-butyl-dimethyl-silanyloxymethyl)-pent-4-enyloxy]-2-phenyl-[1,3]dioxane

Chemical Property of (2R,4S,5R)-4-Allyl-5-[(1S,2R)-2-(tert-butyl-dimethyl-silanyloxy)-1-(tert-butyl-dimethyl-silanyloxymethyl)-pent-4-enyloxy]-2-phenyl-[1,3]dioxane

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2R,4S,5R)-4-Allyl-5-[(1S,2R)-2-(tert-butyl-dimethyl-silanyloxy)-1-(tert-butyl-dimethyl-silanyloxymethyl)-pent-4-enyloxy]-2-phenyl-[1,3]dioxane

There total 17 articles about (2R,4S,5R)-4-Allyl-5-[(1S,2R)-2-(tert-butyl-dimethyl-silanyloxy)-1-(tert-butyl-dimethyl-silanyloxymethyl)-pent-4-enyloxy]-2-phenyl-[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: 99.0%

Methyltriphenylphosphonium bromide (1779-49-3) + {(2R,4S,5R)-5-[(1S,2R)-2-(tert-Butyl-dimethyl-silanyloxy)-1-(tert-butyl-dimethyl-silanyloxymethyl)-pent-4-enyloxy]-2-phenyl-[1,3]dioxan-4-yl}-acetaldehyde (475641-88-4) → (2R,4S,5R)-4-Allyl-5-[(1S,2R)-2-(tert-butyl-dimethyl-silanyloxy)-1-(tert-butyl-dimethyl-silanyloxymethyl)-pent-4-enyloxy]-2-phenyl-[1,3]dioxane (475641-89-5)

Guidance literature:

Methyltriphenylphosphonium bromide; With sodium hexamethyldisilazane; In tetrahydrofuran; at 22 ℃; for 2h;

{(2R,4S,5R)-5-[(1S,2R)-2-(tert-Butyl-dimethyl-silanyloxy)-1-(tert-butyl-dimethyl-silanyloxymethyl)-pent-4-enyloxy]-2-phenyl-[1,3]dioxan-4-yl}-acetaldehyde; In tetrahydrofuran; at -78 - 23 ℃; for 4h;

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) → (2R,4S,5R)-4-Allyl-5-[(1S,2R)-2-(tert-butyl-dimethyl-silanyloxy)-1-(tert-butyl-dimethyl-silanyloxymethyl)-pent-4-enyloxy]-2-phenyl-[1,3]dioxane (475641-89-5)

Guidance literature:

Multi-step reaction with 17 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: 79 percent / CH₂Cl₂ / 3.83 h / -78 - -20 °C

8.1: 95 percent / TBAF / tetrahydrofuran / 22 °C

9.1: aq. NaIO₄ / dioxane / 22 °C

10.1: NaBH₄ / methanol / 0 °C

11.1: 98 percent / benzene / Heating

12.1: 98 percent / 2,6-lutidine / CH₂Cl₂ / 21 - 23 °C

13.1: aq. H₂O₂ / ethyl acetate / 2 h / 21 - 23 °C

14.1: 2,6-lutidine / CH₂Cl₂ / 21 - 25 °C

15.1: 96 percent / dimethylsulfoxide / 23 - 25 °C

16.1: 88 percent / DIBALH / CH₂Cl₂ / -78 °C

17.1: NaHMDS / tetrahydrofuran / 2 h / 22 °C

17.2: 99 percent / tetrahydrofuran / 4 h / -78 - 23 °C

With 2,6-dimethylpyridine; hydrogenchloride; sodium tetrahydroborate; sodium periodate; osmium(VIII) oxide; N-methyl-2-indolinone; Amberlyst 15; tetrabutyl ammonium fluoride; dihydrogen peroxide; sodium hexamethyldisilazane; diisobutylaluminium hydride; In tetrahydrofuran; 1,4-dioxane; methanol; dichloromethane; chloroform; dimethyl sulfoxide; ethyl acetate; benzene; 17.2: Wittig reaction;

DOI:10.1055/s-2002-33527

Reference yield:

2,3-dideoxy-α-D-erythro-hex-2-enopyranosyl cyanide (88180-36-3) → (2R,4S,5R)-4-Allyl-5-[(1S,2R)-2-(tert-butyl-dimethyl-silanyloxy)-1-(tert-butyl-dimethyl-silanyloxymethyl)-pent-4-enyloxy]-2-phenyl-[1,3]dioxane (475641-89-5)

Guidance literature:

Multi-step reaction with 16 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: 79 percent / CH₂Cl₂ / 3.83 h / -78 - -20 °C

7.1: 95 percent / TBAF / tetrahydrofuran / 22 °C

8.1: aq. NaIO₄ / dioxane / 22 °C

9.1: NaBH₄ / methanol / 0 °C

10.1: 98 percent / benzene / Heating

11.1: 98 percent / 2,6-lutidine / CH₂Cl₂ / 21 - 23 °C

12.1: aq. H₂O₂ / ethyl acetate / 2 h / 21 - 23 °C

13.1: 2,6-lutidine / CH₂Cl₂ / 21 - 25 °C

14.1: 96 percent / dimethylsulfoxide / 23 - 25 °C

15.1: 88 percent / DIBALH / CH₂Cl₂ / -78 °C

16.1: NaHMDS / tetrahydrofuran / 2 h / 22 °C

16.2: 99 percent / tetrahydrofuran / 4 h / -78 - 23 °C

With 2,6-dimethylpyridine; hydrogenchloride; sodium tetrahydroborate; sodium periodate; osmium(VIII) oxide; N-methyl-2-indolinone; Amberlyst 15; tetrabutyl ammonium fluoride; dihydrogen peroxide; sodium hexamethyldisilazane; diisobutylaluminium hydride; In tetrahydrofuran; 1,4-dioxane; methanol; dichloromethane; chloroform; dimethyl sulfoxide; ethyl acetate; benzene; 16.2: Wittig reaction;

DOI:10.1055/s-2002-33527

upstream raw materials:

Methyltriphenylphosphonium bromide

{(2R,4S,5R)-5-[(1S,2R)-2-(tert-Butyl-dimethyl-silanyloxy)-1-(tert-butyl-dimethyl-silanyloxymethyl)-pent-4-enyloxy]-2-phenyl-[1,3]dioxan-4-yl}-acetaldehyde

((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

Downstream raw materials:

(Z)-(2R,4aR,6S,7R,11aS)-7-(tert-Butyl-dimethyl-silanyloxy)-6-(tert-butyl-dimethyl-silanyloxymethyl)-2-phenyl-4a,6,7,8,11,11a-hexahydro-4H-1,3,5-trioxa-benzocyclononene