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

Base Information

• Chemical Name: (2S,3R)-2-[(2R,4S,5R)-4-(2-Methyl-allyl)-2-phenyl-[1,3]dioxan-5-yloxy]-pent-4-ene-1,3-diol
• CAS No.: 475641-93-1
• Molecular Formula: C₁₉H₂₆O₅
• Molecular Weight: 334.412
• Mol file: 475641-93-1.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 21 articles about (2S,3R)-2-[(2R,4S,5R)-4-(2-Methyl-allyl)-2-phenyl-[1,3]dioxan-5-yloxy]-pent-4-ene-1,3-diol 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: 100.0%

(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) → (2S,3R)-2-[(2R,4S,5R)-4-(2-Methyl-allyl)-2-phenyl-[1,3]dioxan-5-yloxy]-pent-4-ene-1,3-diol (475641-93-1)

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 23 ℃; for 14h;

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) → (2S,3R)-2-[(2R,4S,5R)-4-(2-Methyl-allyl)-2-phenyl-[1,3]dioxan-5-yloxy]-pent-4-ene-1,3-diol (475641-93-1)

Guidance literature:

Multi-step reaction with 20 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

20.1: 100 percent / TBAF / tetrahydrofuran / 14 h / 23 °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) → (2S,3R)-2-[(2R,4S,5R)-4-(2-Methyl-allyl)-2-phenyl-[1,3]dioxan-5-yloxy]-pent-4-ene-1,3-diol (475641-93-1)

Guidance literature:

Multi-step reaction with 19 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

19.1: 100 percent / TBAF / tetrahydrofuran / 14 h / 23 °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:

(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

((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:

(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

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