(R)-2-[(2S,4aS,5R,6R,7R,8aS,9aR,10aS)-6-Benzyloxy-7-(2-benzyloxy-ethyl)-5-methoxymethoxy-10a-methyl-3-methylene-decahydro-1,8,10-trioxa-anthracen-2-yl]-propane-1,2-diol

Base Information

• Chemical Name: (R)-2-[(2S,4aS,5R,6R,7R,8aS,9aR,10aS)-6-Benzyloxy-7-(2-benzyloxy-ethyl)-5-methoxymethoxy-10a-methyl-3-methylene-decahydro-1,8,10-trioxa-anthracen-2-yl]-propane-1,2-diol
• CAS No.: 912281-31-3
• Molecular Formula: C₃₄H₄₆O₉
• Molecular Weight: 598.734

Synonyms:(R)-2-[(2S,4aS,5R,6R,7R,8aS,9aR,10aS)-6-Benzyloxy-7-(2-benzyloxy-ethyl)-5-methoxymethoxy-10a-methyl-3-methylene-decahydro-1,8,10-trioxa-anthracen-2-yl]-propane-1,2-diol

Chemical Property of (R)-2-[(2S,4aS,5R,6R,7R,8aS,9aR,10aS)-6-Benzyloxy-7-(2-benzyloxy-ethyl)-5-methoxymethoxy-10a-methyl-3-methylene-decahydro-1,8,10-trioxa-anthracen-2-yl]-propane-1,2-diol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (R)-2-[(2S,4aS,5R,6R,7R,8aS,9aR,10aS)-6-Benzyloxy-7-(2-benzyloxy-ethyl)-5-methoxymethoxy-10a-methyl-3-methylene-decahydro-1,8,10-trioxa-anthracen-2-yl]-propane-1,2-diol

There total 25 articles about (R)-2-[(2S,4aS,5R,6R,7R,8aS,9aR,10aS)-6-Benzyloxy-7-(2-benzyloxy-ethyl)-5-methoxymethoxy-10a-methyl-3-methylene-decahydro-1,8,10-trioxa-anthracen-2-yl]-propane-1,2-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: 84.0%

(2S,3R,4aS,6R,7R,8R,8aS)-7-Benzyloxy-6-(2-benzyloxy-ethyl)-2-[2-((2R,3R)-3-hydroxymethyl-3-methyl-oxiranyl)-allyl]-8-methoxymethoxy-8a-methyl-octahydro-pyrano[3,2-b]pyran-3-ol (912281-30-2) → (R)-2-[(2S,4aS,5R,6R,7R,8aS,9aR,10aS)-6-Benzyloxy-7-(2-benzyloxy-ethyl)-5-methoxymethoxy-10a-methyl-3-methylene-decahydro-1,8,10-trioxa-anthracen-2-yl]-propane-1,2-diol (912281-31-3)

Guidance literature:

With camphor-10-sulfonic acid; In dichloromethane; at 0 ℃;

DOI:10.1016/j.tetlet.2006.07.027

Reference yield:

tert-Butyl-dimethyl-((2R,4aR,6S,7R,8aS)-4a-methyl-2-phenyl-6-vinyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yloxy)-silane (912281-33-5) → (R)-2-[(2S,4aS,5R,6R,7R,8aS,9aR,10aS)-6-Benzyloxy-7-(2-benzyloxy-ethyl)-5-methoxymethoxy-10a-methyl-3-methylene-decahydro-1,8,10-trioxa-anthracen-2-yl]-propane-1,2-diol (912281-31-3)

Guidance literature:

Multi-step reaction with 24 steps

1.1: thexylborane / tetrahydrofuran / 0 °C

1.2: 89 percent / aq. NaOH; H₂O₂

2.1: 99 percent / imidazole / dimethylformamide / 0 °C

3.1: 100 percent / H₂ / Pd(OH)2/C / 20 °C

4.1: 84 percent / KH / tetrahydrofuran / 0 - 20 °C

5.1: TMSI; HMDS / CH₂Cl₂ / 0 °C

5.2: 92 percent / K₂CO₃ / methanol / 20 °C

6.1: (COCl)2; DMSO; Et₃N / CH₂Cl₂ / -78 - 20 °C

7.1: n-BuLi / tetrahydrofuran / -78 °C

8.1: iPr₂NEt / CH₂Cl₂ / Heating

9.1: DDQ; NaHCO₃ / CH₂Cl₂ / 20 °C

10.1: N-methylmorpholine / CH₂Cl₂ / 20 °C

11.1: 82 percent / MeI; NaHCO₃ / CH₂Cl₂ / Heating

12.1: 79 percent / SmI₂ / methanol; tetrahydrofuran / -78 °C

13.1: LiAlH₄ / diethyl ether / 0 °C

14.1: NaH / tetrahydrofuran / Heating

15.1: 90 percent / CSA / methanol / 0 °C

16.1: 100 percent / I₂; PPh₃; imidazole / benzene; diethyl ether

17.1: 97 percent / dimethylformamide / 50 °C

18.1: 81 percent / DIBAL-H / CH₂Cl₂ / -78 °C

19.1: Et₃N / CH₂Cl₂ / 20 °C

20.1: CH₂Cl₂ / 20 °C

21.1: 96 percent / DIBAL-H / CH₂Cl₂ / -78 °C

22.1: 100 percent / (-)-DET; Ti(OiPr)4; TBHP / molecular sieves 4 Angstroem / CH₂Cl₂ / -20 °C

23.1: 100 percent / TBAF / tetrahydrofuran / 20 °C

24.1: 84 percent / CSA / CH₂Cl₂ / 0 °C

With 4-methyl-morpholine; 1H-imidazole; titanium(IV) isopropylate; tert.-butylhydroperoxide; lithium aluminium tetrahydride; n-butyllithium; samarium diiodide; oxalyl dichloride; trimethylsilyl iodide; thexylborane; camphor-10-sulfonic acid; tetrabutyl ammonium fluoride; hydrogen; iodine; potassium hydride; sodium hydride; diisobutylaluminium hydride; sodium hydrogencarbonate; dimethyl sulfoxide; (-)-diethyl tartrate; triethylamine; N-ethyl-N,N-diisopropylamine; triphenylphosphine; 1,1,1,3,3,3-hexamethyl-disilazane; 2,3-dicyano-5,6-dichloro-p-benzoquinone; methyl iodide; palladium dihydroxide; 4 A molecular sieve; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; N,N-dimethyl-formamide; benzene; 6.1: Swern oxidation / 20.1: Wittig olefination / 22.1: Sharpless epoxidation;

DOI:10.1016/j.tetlet.2006.07.027

Reference yield:

2-[(2R,4aR,6S,7R,8aS)-7-(tert-Butyl-dimethyl-silanyloxy)-4a-methyl-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-6-yl]-ethanol (912281-34-6) → (R)-2-[(2S,4aS,5R,6R,7R,8aS,9aR,10aS)-6-Benzyloxy-7-(2-benzyloxy-ethyl)-5-methoxymethoxy-10a-methyl-3-methylene-decahydro-1,8,10-trioxa-anthracen-2-yl]-propane-1,2-diol (912281-31-3)

Guidance literature:

Multi-step reaction with 23 steps

1.1: 99 percent / imidazole / dimethylformamide / 0 °C

2.1: 100 percent / H₂ / Pd(OH)2/C / 20 °C

3.1: 84 percent / KH / tetrahydrofuran / 0 - 20 °C

4.1: TMSI; HMDS / CH₂Cl₂ / 0 °C

4.2: 92 percent / K₂CO₃ / methanol / 20 °C

5.1: (COCl)2; DMSO; Et₃N / CH₂Cl₂ / -78 - 20 °C

6.1: n-BuLi / tetrahydrofuran / -78 °C

7.1: iPr₂NEt / CH₂Cl₂ / Heating

8.1: DDQ; NaHCO₃ / CH₂Cl₂ / 20 °C

9.1: N-methylmorpholine / CH₂Cl₂ / 20 °C

10.1: 82 percent / MeI; NaHCO₃ / CH₂Cl₂ / Heating

11.1: 79 percent / SmI₂ / methanol; tetrahydrofuran / -78 °C

12.1: LiAlH₄ / diethyl ether / 0 °C

13.1: NaH / tetrahydrofuran / Heating

14.1: 90 percent / CSA / methanol / 0 °C

15.1: 100 percent / I₂; PPh₃; imidazole / benzene; diethyl ether

16.1: 97 percent / dimethylformamide / 50 °C

17.1: 81 percent / DIBAL-H / CH₂Cl₂ / -78 °C

18.1: Et₃N / CH₂Cl₂ / 20 °C

19.1: CH₂Cl₂ / 20 °C

20.1: 96 percent / DIBAL-H / CH₂Cl₂ / -78 °C

21.1: 100 percent / (-)-DET; Ti(OiPr)4; TBHP / molecular sieves 4 Angstroem / CH₂Cl₂ / -20 °C

22.1: 100 percent / TBAF / tetrahydrofuran / 20 °C

23.1: 84 percent / CSA / CH₂Cl₂ / 0 °C

With 4-methyl-morpholine; 1H-imidazole; titanium(IV) isopropylate; tert.-butylhydroperoxide; lithium aluminium tetrahydride; n-butyllithium; samarium diiodide; oxalyl dichloride; trimethylsilyl iodide; camphor-10-sulfonic acid; tetrabutyl ammonium fluoride; hydrogen; iodine; potassium hydride; sodium hydride; diisobutylaluminium hydride; sodium hydrogencarbonate; dimethyl sulfoxide; (-)-diethyl tartrate; triethylamine; N-ethyl-N,N-diisopropylamine; triphenylphosphine; 1,1,1,3,3,3-hexamethyl-disilazane; 2,3-dicyano-5,6-dichloro-p-benzoquinone; methyl iodide; palladium dihydroxide; 4 A molecular sieve; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; N,N-dimethyl-formamide; benzene; 5.1: Swern oxidation / 19.1: Wittig olefination / 21.1: Sharpless epoxidation;

DOI:10.1016/j.tetlet.2006.07.027

upstream raw materials:

(2S,3R,4aS,6R,7R,8R,8aS)-7-Benzyloxy-6-(2-benzyloxy-ethyl)-2-[2-((2R,3R)-3-hydroxymethyl-3-methyl-oxiranyl)-allyl]-8-methoxymethoxy-8a-methyl-octahydro-pyrano[3,2-b]pyran-3-ol

tert-Butyl-dimethyl-((2R,4aR,6S,7R,8aS)-4a-methyl-2-phenyl-6-vinyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yloxy)-silane

2-[(2R,4aR,6S,7R,8aS)-7-(tert-Butyl-dimethyl-silanyloxy)-4a-methyl-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-6-yl]-ethanol

5-(tert-butyl-dimethyl-silanyloxy)-6-[2-(tert-butyl-dimethyl-silanyloxy)-ethyl]-2-hydroxymethyl-2-methyl-tetrahydro-pyran-3-ol

Downstream raw materials:

4-Bromo-benzoic acid (R)-2-[(2S,4aS,5R,6R,7R,8aS,9aR,10aS)-6-benzyloxy-7-(2-benzyloxy-ethyl)-5-methoxymethoxy-10a-methyl-3-methylene-decahydro-1,8,10-trioxa-anthracen-2-yl]-2-hydroxy-propyl ester

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