1-[(2S,3S,4R,4aR,5aR,9R,10aS,11aR)-3,4-Bis-benzyloxy-9-(2-hydroxy-ethyl)-7-triethylsilanyl-2,3,4,4a,5a,6,9,10a,11,11a-decahydro-1,5,10-trioxa-cyclohepta[b]naphthalen-2-yl]-propan-2-one

Base Information

• Chemical Name: 1-[(2S,3S,4R,4aR,5aR,9R,10aS,11aR)-3,4-Bis-benzyloxy-9-(2-hydroxy-ethyl)-7-triethylsilanyl-2,3,4,4a,5a,6,9,10a,11,11a-decahydro-1,5,10-trioxa-cyclohepta[b]naphthalen-2-yl]-propan-2-one
• CAS No.: 440339-80-0
• Molecular Formula: C₃₇H₅₂O₇Si
• Molecular Weight: 636.901
• Mol file: 440339-80-0.mol

Synonyms:1-[(2S,3S,4R,4aR,5aR,9R,10aS,11aR)-3,4-Bis-benzyloxy-9-(2-hydroxy-ethyl)-7-triethylsilanyl-2,3,4,4a,5a,6,9,10a,11,11a-decahydro-1,5,10-trioxa-cyclohepta[b]naphthalen-2-yl]-propan-2-one

Chemical Property of 1-[(2S,3S,4R,4aR,5aR,9R,10aS,11aR)-3,4-Bis-benzyloxy-9-(2-hydroxy-ethyl)-7-triethylsilanyl-2,3,4,4a,5a,6,9,10a,11,11a-decahydro-1,5,10-trioxa-cyclohepta[b]naphthalen-2-yl]-propan-2-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 1-[(2S,3S,4R,4aR,5aR,9R,10aS,11aR)-3,4-Bis-benzyloxy-9-(2-hydroxy-ethyl)-7-triethylsilanyl-2,3,4,4a,5a,6,9,10a,11,11a-decahydro-1,5,10-trioxa-cyclohepta[b]naphthalen-2-yl]-propan-2-one

There total 28 articles about 1-[(2S,3S,4R,4aR,5aR,9R,10aS,11aR)-3,4-Bis-benzyloxy-9-(2-hydroxy-ethyl)-7-triethylsilanyl-2,3,4,4a,5a,6,9,10a,11,11a-decahydro-1,5,10-trioxa-cyclohepta[b]naphthalen-2-yl]-propan-2-one 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: 83.0%

2-((2S,3S,4R,4aR,5aR,9R,10aS,11aR)-2-Allyl-3,4-bis-benzyloxy-7-triethylsilanyl-2,3,4,4a,5a,6,9,10a,11,11a-decahydro-1,5,10-trioxa-cyclohepta[b]naphthalen-9-yl)-ethanol (344315-31-7) → 1-[(2S,3S,4R,4aR,5aR,9R,10aS,11aR)-3,4-Bis-benzyloxy-9-(2-hydroxy-ethyl)-7-triethylsilanyl-2,3,4,4a,5a,6,9,10a,11,11a-decahydro-1,5,10-trioxa-cyclohepta[b]naphthalen-2-yl]-propan-2-one (440339-80-0)

Guidance literature:

With oxygen; copper(l) chloride; palladium dichloride; In water; N,N-dimethyl-formamide; at 20 ℃; for 48h;

DOI:10.1016/S0040-4020(02)00044-3

Reference yield:

methyl 2,3-di-O-benzyl-4,6-O-isopropylidene-α-D-glucopyranoside (76491-08-2) → 1-[(2S,3S,4R,4aR,5aR,9R,10aS,11aR)-3,4-Bis-benzyloxy-9-(2-hydroxy-ethyl)-7-triethylsilanyl-2,3,4,4a,5a,6,9,10a,11,11a-decahydro-1,5,10-trioxa-cyclohepta[b]naphthalen-2-yl]-propan-2-one (440339-80-0)

Guidance literature:

Multi-step reaction with 26 steps

1.1: 117 g / Amberlyst-15E / methanol / 18 h / 20 °C

2.1: 85 percent / imidazole; PPh₃; I₂ / toluene / 2 h / 20 °C

3.1: DMAP / CH₂Cl₂ / 48 h / 20 °C

4.1: Ac₂O; aq. H₂SO₄ / 0.25 h / -5 - 0 °C

4.2: aq. HCl / tetrahydrofuran / 168 h / 20 °C

4.3: 61.0 g / Ac₂O / dimethylsulfoxide / 12 h / 20 °C

5.1: tetrahydrofuran; diethyl ether / 1 h / -78 °C

5.2: 85 percent / Et₃SiH; BF₃*OEt₂ / acetonitrile / 0.5 h / -10 - 0 °C

6.1: 23.69 g / DIBAL / toluene; CH₂Cl₂ / 1 h / -78 °C

7.1: pyridinium p-toluenesulfonate / CH₂Cl₂ / 12 h / 20 °C

8.1: 20.27 g / dimethylsulfoxide / 1 h / 65 °C

9.1: 98 percent / DIBAL / CH₂Cl₂ / 1 h / -78 - -20 °C

10.1: n-BuLi / tetrahydrofuran; hexane / 0.33 h / 0 °C

10.2: tetrahydrofuran; hexane / 0.67 h / 0 °C

11.1: pyridine / 12 h / 20 °C

12.1: 6.39 g / Amberlyst-15E / methanol / 48 h / 20 °C

13.1: 100 percent / pyridine / CH₂Cl₂ / 20 °C

14.1: (CF₃CO₂)2IPh; H₂O / acetonitrile / 0.25 h / 20 °C

14.2: 72 percent / Et₃SiH; BF₃*OEt₂ / acetonitrile / 1 h / 0 °C

15.1: K₂CO₃ / methanol / 20 h / 20 °C

16.1: 3.37 g / IBX / dimethylsulfoxide / 12 h / 20 °C

17.1: Et₃N / methanol / 12 h / 20 °C

17.2: 87 percent / NaBH₄ / methanol; CH₂Cl₂ / 1 h / -78 °C

18.1: pyridinium p-toluenesulfonate / CH₂Cl₂ / 12 h / 20 °C

19.1: 643 mg / NaOMe / methanol / 12 h / 45 °C

20.1: 96 percent / IBX / dimethylsulfoxide / 12 h / 20 °C

21.1: PPh₃ / CH₂Cl₂ / 0.17 h / 0 °C

21.2: CH₂Cl₂ / 0.5 h / 0 °C

22.1: 2.57 g / pyridinium p-toluenesulfonate / CH₂Cl₂ / 6 h / 20 °C

23.1: n-BuLi / tetrahydrofuran; hexane / 0.25 h / -78 °C

23.2: tetrahydrofuran; hexane / 1 h / -78 - 0 °C

24.1: 3.45 g / Amberlyst-15E / methanol / 2 h / 20 °C

25.1: Co₂(CO)8 / CH₂Cl₂ / 0.33 h / 20 °C

25.2: BF₃*OEt₂ / CH₂Cl₂ / 0.25 h / 20 °C

25.3: EtOH / 1,2-dichloro-ethane / 60 °C

26.1: 83 percent / O₂; CuCl; PdCl₂ / dimethylformamide; H₂O / 48 h / 20 °C

With pyridine; 1H-imidazole; dmap; n-butyllithium; dicobalt octacarbonyl; Amberlyst-15E; sulfuric acid; water; iodine; oxygen; sodium methylate; pyridinium p-toluenesulfonate; acetic anhydride; diisobutylaluminium hydride; potassium carbonate; triethylamine; triphenylphosphine; bis-[(trifluoroacetoxy)iodo]benzene; copper(l) chloride; palladium dichloride; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione; In tetrahydrofuran; methanol; diethyl ether; hexane; dichloromethane; water; dimethyl sulfoxide; N,N-dimethyl-formamide; toluene; acetonitrile; 26.1: Wacker oxidation;

DOI:10.1016/S0040-4020(02)00044-3

Reference yield:

methyl 6-deoxy-6-iodo-2,3-bis-O-(phenylmethyl)-α-D-glucopyranoside (87326-88-3) → 1-[(2S,3S,4R,4aR,5aR,9R,10aS,11aR)-3,4-Bis-benzyloxy-9-(2-hydroxy-ethyl)-7-triethylsilanyl-2,3,4,4a,5a,6,9,10a,11,11a-decahydro-1,5,10-trioxa-cyclohepta[b]naphthalen-2-yl]-propan-2-one (440339-80-0)

Guidance literature:

Multi-step reaction with 24 steps

1.1: DMAP / CH₂Cl₂ / 48 h / 20 °C

2.1: Ac₂O; aq. H₂SO₄ / 0.25 h / -5 - 0 °C

2.2: aq. HCl / tetrahydrofuran / 168 h / 20 °C

2.3: 61.0 g / Ac₂O / dimethylsulfoxide / 12 h / 20 °C

3.1: tetrahydrofuran; diethyl ether / 1 h / -78 °C

3.2: 85 percent / Et₃SiH; BF₃*OEt₂ / acetonitrile / 0.5 h / -10 - 0 °C

4.1: 23.69 g / DIBAL / toluene; CH₂Cl₂ / 1 h / -78 °C

5.1: pyridinium p-toluenesulfonate / CH₂Cl₂ / 12 h / 20 °C

6.1: 20.27 g / dimethylsulfoxide / 1 h / 65 °C

7.1: 98 percent / DIBAL / CH₂Cl₂ / 1 h / -78 - -20 °C

8.1: n-BuLi / tetrahydrofuran; hexane / 0.33 h / 0 °C

8.2: tetrahydrofuran; hexane / 0.67 h / 0 °C

9.1: pyridine / 12 h / 20 °C

10.1: 6.39 g / Amberlyst-15E / methanol / 48 h / 20 °C

11.1: 100 percent / pyridine / CH₂Cl₂ / 20 °C

12.1: (CF₃CO₂)2IPh; H₂O / acetonitrile / 0.25 h / 20 °C

12.2: 72 percent / Et₃SiH; BF₃*OEt₂ / acetonitrile / 1 h / 0 °C

13.1: K₂CO₃ / methanol / 20 h / 20 °C

14.1: 3.37 g / IBX / dimethylsulfoxide / 12 h / 20 °C

15.1: Et₃N / methanol / 12 h / 20 °C

15.2: 87 percent / NaBH₄ / methanol; CH₂Cl₂ / 1 h / -78 °C

16.1: pyridinium p-toluenesulfonate / CH₂Cl₂ / 12 h / 20 °C

17.1: 643 mg / NaOMe / methanol / 12 h / 45 °C

18.1: 96 percent / IBX / dimethylsulfoxide / 12 h / 20 °C

19.1: PPh₃ / CH₂Cl₂ / 0.17 h / 0 °C

19.2: CH₂Cl₂ / 0.5 h / 0 °C

20.1: 2.57 g / pyridinium p-toluenesulfonate / CH₂Cl₂ / 6 h / 20 °C

21.1: n-BuLi / tetrahydrofuran; hexane / 0.25 h / -78 °C

21.2: tetrahydrofuran; hexane / 1 h / -78 - 0 °C

22.1: 3.45 g / Amberlyst-15E / methanol / 2 h / 20 °C

23.1: Co₂(CO)8 / CH₂Cl₂ / 0.33 h / 20 °C

23.2: BF₃*OEt₂ / CH₂Cl₂ / 0.25 h / 20 °C

23.3: EtOH / 1,2-dichloro-ethane / 60 °C

24.1: 83 percent / O₂; CuCl; PdCl₂ / dimethylformamide; H₂O / 48 h / 20 °C

With pyridine; dmap; n-butyllithium; dicobalt octacarbonyl; Amberlyst-15E; sulfuric acid; water; oxygen; sodium methylate; pyridinium p-toluenesulfonate; acetic anhydride; diisobutylaluminium hydride; potassium carbonate; triethylamine; triphenylphosphine; bis-[(trifluoroacetoxy)iodo]benzene; copper(l) chloride; palladium dichloride; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione; In tetrahydrofuran; methanol; diethyl ether; hexane; dichloromethane; water; dimethyl sulfoxide; N,N-dimethyl-formamide; toluene; acetonitrile; 24.1: Wacker oxidation;

DOI:10.1016/S0040-4020(02)00044-3

upstream raw materials:

2-((2S,3S,4R,4aR,5aR,9R,10aS,11aR)-2-Allyl-3,4-bis-benzyloxy-7-triethylsilanyl-2,3,4,4a,5a,6,9,10a,11,11a-decahydro-1,5,10-trioxa-cyclohepta[b]naphthalen-9-yl)-ethanol

methyl 2,3-di-O-benzyl-4,6-O-isopropylidene-α-D-glucopyranoside

methyl 6-deoxy-6-iodo-2,3-bis-O-(phenylmethyl)-α-D-glucopyranoside

methyl-alpha-D-glucopyranoside

Downstream raw materials:

C₃₈H₅₂O₉Si

(3aR,4aS,5aR,7S,8S,9R,9aR,10aR,12S,12aS)-8,9-Bis-benzyloxy-12-iodo-7-(2-methyl-[1,3]dithian-2-ylmethyl)-12-triethylsilanyl-dodecahydro-1,4,6,10-tetraoxa-naphtho[2,3-f]azulen-2-one

C₄₁H₅₆O₆S₂Si

C₄₀H₅₆O₇S₂Si