(2R,3S,4aR,6S,7R,9R,9aS)-6-Allyl-7-((2R,3S)-2-allyl-tetrahydro-pyran-3-yloxy)-3,9-bis-benzyloxy-2-benzyloxymethyl-9a-methyl-octahydro-1,5-dioxa-benzocycloheptene

Base Information

• Chemical Name: (2R,3S,4aR,6S,7R,9R,9aS)-6-Allyl-7-((2R,3S)-2-allyl-tetrahydro-pyran-3-yloxy)-3,9-bis-benzyloxy-2-benzyloxymethyl-9a-methyl-octahydro-1,5-dioxa-benzocycloheptene
• CAS No.: 220864-30-2
• Molecular Formula: C₄₃H₅₄O₇
• Molecular Weight: 682.898
• Mol file: 220864-30-2.mol

Synonyms:(2R,3S,4aR,6S,7R,9R,9aS)-6-Allyl-7-((2R,3S)-2-allyl-tetrahydro-pyran-3-yloxy)-3,9-bis-benzyloxy-2-benzyloxymethyl-9a-methyl-octahydro-1,5-dioxa-benzocycloheptene

Chemical Property of (2R,3S,4aR,6S,7R,9R,9aS)-6-Allyl-7-((2R,3S)-2-allyl-tetrahydro-pyran-3-yloxy)-3,9-bis-benzyloxy-2-benzyloxymethyl-9a-methyl-octahydro-1,5-dioxa-benzocycloheptene

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2R,3S,4aR,6S,7R,9R,9aS)-6-Allyl-7-((2R,3S)-2-allyl-tetrahydro-pyran-3-yloxy)-3,9-bis-benzyloxy-2-benzyloxymethyl-9a-methyl-octahydro-1,5-dioxa-benzocycloheptene

There total 28 articles about (2R,3S,4aR,6S,7R,9R,9aS)-6-Allyl-7-((2R,3S)-2-allyl-tetrahydro-pyran-3-yloxy)-3,9-bis-benzyloxy-2-benzyloxymethyl-9a-methyl-octahydro-1,5-dioxa-benzocycloheptene 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%

(2R,3S,4aR,6S,7R,9R,9aS)-6-Allyl-3,9-bis-benzyloxy-2-benzyloxymethyl-9a-methyl-7-((2R,3S)-2-prop-2-ynyl-tetrahydro-pyran-3-yloxy)-octahydro-1,5-dioxa-benzocycloheptene (220864-41-5) → (2R,3S,4aR,6S,7R,9R,9aS)-6-Allyl-7-((2R,3S)-2-allyl-tetrahydro-pyran-3-yloxy)-3,9-bis-benzyloxy-2-benzyloxymethyl-9a-methyl-octahydro-1,5-dioxa-benzocycloheptene (220864-30-2)

Guidance literature:

With hydrogen; Lindlar's catalyst; In ethyl acetate; at 20 ℃; for 13h;

DOI:10.1021/jo010974p

Reference yield:

(2R,3S)-2-hydroxymethyltetrahydropyran-3-ol (51450-45-4) → (2R,3S,4aR,6S,7R,9R,9aS)-6-Allyl-7-((2R,3S)-2-allyl-tetrahydro-pyran-3-yloxy)-3,9-bis-benzyloxy-2-benzyloxymethyl-9a-methyl-octahydro-1,5-dioxa-benzocycloheptene (220864-30-2)

Guidance literature:

Multi-step reaction with 13 steps

1.1: 1.33 g / Sc(OTf)3 / benzene / 20 °C

2.1: 70 percent / CH₂Cl₂; hexane / 2 h / 20 °C

3.1: i-Pr₂NEt / CH₂Cl₂ / 20 °C

4.1: TBAF / tetrahydrofuran / 20 °C

5.1: N-methylmorpholine / CH₂Cl₂ / 20 °C

6.1: 76 percent / n-Bu₃SnH; AIBN / toluene / 80 °C

7.1: DIBALH / CH₂Cl₂; toluene / 1 h / -78 °C

8.1: sodium bis(trimethylsilyl)amide / tetrahydrofuran / 0.5 h / 0 °C

8.2: 24.5 mg / tetrahydrofuran / 0.5 h / 0 °C

9.1: 83 percent / Me₂S; BF₃*Et₂O / CH₂Cl₂ / 1 h / 20 °C

10.1: 2,6-lutidine / CH₂Cl₂ / 1 h / -78 °C

11.1: n-BuLi; HMPA / tetrahydrofuran / 0.33 h / -78 °C

11.2: 9.3 mg / tetrahydrofuran / 20 h / -78 °C

12.1: 90 percent / K₂CO₃ / methanol; tetrahydrofuran / 10 h / 20 °C

13.1: 88 percent / H₂ / Lindlar catalyst / ethyl acetate / 13 h / 20 °C

With 4-methyl-morpholine; 2,6-dimethylpyridine; N,N,N,N,N,N-hexamethylphosphoric triamide; n-butyllithium; dimethylsulfide; 2,2'-azobis(isobutyronitrile); boron trifluoride diethyl etherate; tetrabutyl ammonium fluoride; hydrogen; tri-n-butyl-tin hydride; sodium hexamethyldisilazane; diisobutylaluminium hydride; potassium carbonate; N-ethyl-N,N-diisopropylamine; scandium tris(trifluoromethanesulfonate); Lindlar's catalyst; In tetrahydrofuran; methanol; hexane; dichloromethane; ethyl acetate; toluene; benzene; 8.2: Wittig reaction;

DOI:10.1021/jo010974p

Reference yield:

(2R,4aR,6S,7R,8aS)-6-Methyl-2-phenyl-6-vinyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-ol (131310-61-7) → (2R,3S,4aR,6S,7R,9R,9aS)-6-Allyl-7-((2R,3S)-2-allyl-tetrahydro-pyran-3-yloxy)-3,9-bis-benzyloxy-2-benzyloxymethyl-9a-methyl-octahydro-1,5-dioxa-benzocycloheptene (220864-30-2)

Guidance literature:

Multi-step reaction with 22 steps

1.1: 2,6-lutidine / CH₂Cl₂ / 14 h / 20 °C

2.1: p-toluenesulfonic acid hydrate / methanol; CH₂Cl₂ / 19.5 h / 20 °C

3.1: NaH / dimethylformamide / 0.25 h / 20 °C

3.2: 35.53 g / dimethylformamide / 16 h / 20 °C

4.1: 5.53 g / aq. OsO₄; N-methylmorpholine N-oxide / acetone / 19 h / 20 °C

5.1: NaIO₄ / tetrahydrofuran; H₂O / 9 h / 20 °C

6.1: 5.24 g / MgBr₂*Et₂O / CH₂Cl₂ / 2 h / -78 - 20 °C

7.1: NaH / dimethylformamide / 0.5 h / 20 °C

7.2: 100 percent / dimethylformamide / 4.5 h / 0 °C

8.1: osmiumm tetraxide; N-methylmorpholine N-oxide / acetone; H₂O / 9 h / 20 °C

9.1: NaIO₄ / tetrahydrofuran; H₂O / 1 h / 20 °C

10.1: 1.33 g / Sc(OTf)3 / benzene / 20 °C

11.1: 70 percent / CH₂Cl₂; hexane / 2 h / 20 °C

12.1: i-Pr₂NEt / CH₂Cl₂ / 20 °C

13.1: TBAF / tetrahydrofuran / 20 °C

14.1: N-methylmorpholine / CH₂Cl₂ / 20 °C

15.1: 76 percent / n-Bu₃SnH; AIBN / toluene / 80 °C

16.1: DIBALH / CH₂Cl₂; toluene / 1 h / -78 °C

17.1: sodium bis(trimethylsilyl)amide / tetrahydrofuran / 0.5 h / 0 °C

17.2: 24.5 mg / tetrahydrofuran / 0.5 h / 0 °C

18.1: 83 percent / Me₂S; BF₃*Et₂O / CH₂Cl₂ / 1 h / 20 °C

19.1: 2,6-lutidine / CH₂Cl₂ / 1 h / -78 °C

20.1: n-BuLi; HMPA / tetrahydrofuran / 0.33 h / -78 °C

20.2: 9.3 mg / tetrahydrofuran / 20 h / -78 °C

21.1: 90 percent / K₂CO₃ / methanol; tetrahydrofuran / 10 h / 20 °C

22.1: 88 percent / H₂ / Lindlar catalyst / ethyl acetate / 13 h / 20 °C

With 4-methyl-morpholine; 2,6-dimethylpyridine; N,N,N,N,N,N-hexamethylphosphoric triamide; sodium periodate; osmium(VIII) oxide; n-butyllithium; dimethylsulfide; 2,2'-azobis(isobutyronitrile); boron trifluoride diethyl etherate; tetrabutyl ammonium fluoride; hydrogen; tri-n-butyl-tin hydride; sodium hexamethyldisilazane; sodium hydride; diisobutylaluminium hydride; potassium carbonate; toluene-4-sulfonic acid; 4-methylmorpholine N-oxide; N-ethyl-N,N-diisopropylamine; magnesium bromide; scandium tris(trifluoromethanesulfonate); Lindlar's catalyst; In tetrahydrofuran; methanol; hexane; dichloromethane; water; ethyl acetate; N,N-dimethyl-formamide; acetone; toluene; benzene; 17.2: Wittig reaction;

DOI:10.1021/jo010974p

upstream raw materials:

(2R,3S,4aR,6S,7R,9R,9aS)-6-Allyl-3,9-bis-benzyloxy-2-benzyloxymethyl-9a-methyl-7-((2R,3S)-2-prop-2-ynyl-tetrahydro-pyran-3-yloxy)-octahydro-1,5-dioxa-benzocycloheptene

(2R,3S)-2-hydroxymethyltetrahydropyran-3-ol

(2R,4aR,6S,7R,8aS)-6-Methyl-2-phenyl-6-vinyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-ol

benzyl bromide