(2R,4S,5R)-5-[(1S,2R)-2-(tert-Butyl-dimethyl-silanyloxy)-1-(tert-butyl-dimethyl-silanyloxymethyl)-but-3-enyloxy]-4-(2-methyl-allyl)-2-phenyl-[1,3]dioxane

Base Information

• Chemical Name: (2R,4S,5R)-5-[(1S,2R)-2-(tert-Butyl-dimethyl-silanyloxy)-1-(tert-butyl-dimethyl-silanyloxymethyl)-but-3-enyloxy]-4-(2-methyl-allyl)-2-phenyl-[1,3]dioxane
• CAS No.: 475641-92-0
• Molecular Formula: C₃₁H₅₄O₅Si₂
• Molecular Weight: 562.938
• Mol file: 475641-92-0.mol

Synonyms:(2R,4S,5R)-5-[(1S,2R)-2-(tert-Butyl-dimethyl-silanyloxy)-1-(tert-butyl-dimethyl-silanyloxymethyl)-but-3-enyloxy]-4-(2-methyl-allyl)-2-phenyl-[1,3]dioxane

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 19 articles about (2R,4S,5R)-5-[(1S,2R)-2-(tert-Butyl-dimethyl-silanyloxy)-1-(tert-butyl-dimethyl-silanyloxymethyl)-but-3-enyloxy]-4-(2-methyl-allyl)-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: 88.0%

1-{(2R,4S,5R)-5-[(1S,2R)-2-(tert-Butyl-dimethyl-silanyloxy)-1-(tert-butyl-dimethyl-silanyloxymethyl)-but-3-enyloxy]-2-phenyl-[1,3]dioxan-4-yl}-propan-2-one (475641-91-9) → (2R,4S,5R)-5-[(1S,2R)-2-(tert-Butyl-dimethyl-silanyloxy)-1-(tert-butyl-dimethyl-silanyloxymethyl)-but-3-enyloxy]-4-(2-methyl-allyl)-2-phenyl-[1,3]dioxane (475641-92-0)

Guidance literature:

In tetrahydrofuran; at 0 ℃; for 0.0833333h;

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)-5-[(1S,2R)-2-(tert-Butyl-dimethyl-silanyloxy)-1-(tert-butyl-dimethyl-silanyloxymethyl)-but-3-enyloxy]-4-(2-methyl-allyl)-2-phenyl-[1,3]dioxane (475641-92-0)

Guidance literature:

Multi-step reaction with 19 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: 100 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: 95 percent / dimethylsulfoxide / 23 - 25 °C

16.1: 97 percent / DIBALH / CH₂Cl₂ / -78 °C

17.1: 89 percent / diethyl ether / 1.5 h / 0 °C

18.1: 100 percent / DMPI; NaHCO₃ / CH₂Cl₂ / 1 h / 0 - 23 °C

19.1: 88 percent / tetrahydrofuran / 0.08 h / 0 °C

With 2,6-dimethylpyridine; hydrogenchloride; sodium tetrahydroborate; sodium periodate; osmium(VIII) oxide; N-methyl-2-indolinone; Amberlyst 15; dimethyl pimelimidate dihydrochloride; tetrabutyl ammonium fluoride; dihydrogen peroxide; tert.-butyl lithium; diisobutylaluminium hydride; sodium hydrogencarbonate; In tetrahydrofuran; 1,4-dioxane; methanol; diethyl ether; dichloromethane; chloroform; dimethyl sulfoxide; ethyl acetate; benzene;

DOI:10.1055/s-2002-33527

Reference yield:

2,3-dideoxy-α-D-erythro-hex-2-enopyranosyl cyanide (88180-36-3) → (2R,4S,5R)-5-[(1S,2R)-2-(tert-Butyl-dimethyl-silanyloxy)-1-(tert-butyl-dimethyl-silanyloxymethyl)-but-3-enyloxy]-4-(2-methyl-allyl)-2-phenyl-[1,3]dioxane (475641-92-0)

Guidance literature:

Multi-step reaction with 18 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: 100 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: 95 percent / dimethylsulfoxide / 23 - 25 °C

15.1: 97 percent / DIBALH / CH₂Cl₂ / -78 °C

16.1: 89 percent / diethyl ether / 1.5 h / 0 °C

17.1: 100 percent / DMPI; NaHCO₃ / CH₂Cl₂ / 1 h / 0 - 23 °C

18.1: 88 percent / tetrahydrofuran / 0.08 h / 0 °C

With 2,6-dimethylpyridine; hydrogenchloride; sodium tetrahydroborate; sodium periodate; osmium(VIII) oxide; N-methyl-2-indolinone; Amberlyst 15; dimethyl pimelimidate dihydrochloride; tetrabutyl ammonium fluoride; dihydrogen peroxide; tert.-butyl lithium; diisobutylaluminium hydride; sodium hydrogencarbonate; In tetrahydrofuran; 1,4-dioxane; methanol; diethyl ether; dichloromethane; chloroform; dimethyl sulfoxide; ethyl acetate; benzene;

DOI:10.1055/s-2002-33527

upstream raw materials:

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

((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:

(2R,4aR,6S,7R,9S,10aS)-6-(tert-Butyl-diphenyl-silanyloxymethyl)-9-methyl-2-phenyl-octahydro-1,3,5-trioxa-benzocycloocten-7-ol

(3R,4S)-5-(tert-Butyl-diphenyl-silanyloxy)-4-[(2R,4S,5R)-4-(2-methyl-allyl)-2-phenyl-[1,3]dioxan-5-yloxy]-pent-1-en-3-ol

(2S,3R)-2-[(2R,4S,5R)-4-(2-Methyl-allyl)-2-phenyl-[1,3]dioxan-5-yloxy]-pent-4-ene-1,3-diol