[(2R,3R,4S,4aS,6R,7S,8aR)-3,4,7-Tris-benzyloxy-6-(2-methoxy-ethyl)-octahydro-pyrano[3,2-b]pyran-2-yl]-acetonitrile

Base Information

• Chemical Name: [(2R,3R,4S,4aS,6R,7S,8aR)-3,4,7-Tris-benzyloxy-6-(2-methoxy-ethyl)-octahydro-pyrano[3,2-b]pyran-2-yl]-acetonitrile
• CAS No.: 181267-41-4
• Molecular Formula: C₃₄H₃₉NO₆
• Molecular Weight: 557.687

Synonyms:[(2R,3R,4S,4aS,6R,7S,8aR)-3,4,7-Tris-benzyloxy-6-(2-methoxy-ethyl)-octahydro-pyrano[3,2-b]pyran-2-yl]-acetonitrile

Chemical Property of [(2R,3R,4S,4aS,6R,7S,8aR)-3,4,7-Tris-benzyloxy-6-(2-methoxy-ethyl)-octahydro-pyrano[3,2-b]pyran-2-yl]-acetonitrile

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of [(2R,3R,4S,4aS,6R,7S,8aR)-3,4,7-Tris-benzyloxy-6-(2-methoxy-ethyl)-octahydro-pyrano[3,2-b]pyran-2-yl]-acetonitrile

There total 21 articles about [(2R,3R,4S,4aS,6R,7S,8aR)-3,4,7-Tris-benzyloxy-6-(2-methoxy-ethyl)-octahydro-pyrano[3,2-b]pyran-2-yl]-acetonitrile 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:

(2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl)-1-propene (82659-53-8) → [(2R,3R,4S,4aS,6R,7S,8aR)-3,4,7-Tris-benzyloxy-6-(2-methoxy-ethyl)-octahydro-pyrano[3,2-b]pyran-2-yl]-acetonitrile (181267-41-4)

Guidance literature:

Multi-step reaction with 20 steps

1: K₂CO₃ / methanol / 12 h / 23 °C

2: CSA / dimethylformamide / 2 h / 50 °C

3: 90 percent / AgNO₃, pyridine / dimethylformamide / 4 h / 23 °C

4: OsO₄, NMO / 2-methyl-propan-2-ol; tetrahydrofuran; H₂O

5: NaIO₄ / methanol

6: NiCl₂/CrCl₂ / tetrahydrofuran; dimethylsulfoxide / 23 °C

7: 91 percent / pyridine

8: n-Bu₄NF, imidazole / tetrahydrofuran

9: DBU / CH₂Cl₂

10: 83 percent / i-Pr₂NEt / CH₂Cl₂

11: 90 percent / DIBAL / diethyl ether / 1.17 h / -78 - 23 °C

12: pyridine, DMAP / dimethylformamide / 3.17 h / 0 - 23 °C

13: AgNO₃, pyridine / dimethylformamide

14: PPTS / methanol; CH₂Cl₂

15: 89 percent / NaH / tetrahydrofuran / 23 °C

16: n-Bu₄NF / tetrahydrofuran / 12 h / 23 °C

17: NaH, n-Bu₄NI / dimethylformamide / 24 h / 23 °C

18: 83 percent / DIBAL / CH₂Cl₂ / 12.5 h / -78 - 23 °C

19: I₂, Ph₃P, imidazole / benzene / 1 h / 23 °C

20: dimethylformamide / 4 h / 55 °C

With pyridine; 1H-imidazole; chromium dichloride; dmap; sodium periodate; osmium(VIII) oxide; N-methyl-2-indolinone; camphor-10-sulfonic acid; tetrabutyl ammonium fluoride; iodine; pyridinium p-toluenesulfonate; tetra-(n-butyl)ammonium iodide; sodium hydride; diisobutylaluminium hydride; potassium carbonate; silver nitrate; 1,8-diazabicyclo[5.4.0]undec-7-ene; N-ethyl-N,N-diisopropylamine; triphenylphosphine; nickel dichloride; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; water; dimethyl sulfoxide; N,N-dimethyl-formamide; tert-butyl alcohol; benzene;

DOI:10.1021/ja961230+

Reference yield:

(2R,3R,4R,5S,6R)-2-allyl-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol (106756-74-5) → [(2R,3R,4S,4aS,6R,7S,8aR)-3,4,7-Tris-benzyloxy-6-(2-methoxy-ethyl)-octahydro-pyrano[3,2-b]pyran-2-yl]-acetonitrile (181267-41-4)

Guidance literature:

Multi-step reaction with 19 steps

1: CSA / dimethylformamide / 2 h / 50 °C

2: 90 percent / AgNO₃, pyridine / dimethylformamide / 4 h / 23 °C

3: OsO₄, NMO / 2-methyl-propan-2-ol; tetrahydrofuran; H₂O

4: NaIO₄ / methanol

5: NiCl₂/CrCl₂ / tetrahydrofuran; dimethylsulfoxide / 23 °C

6: 91 percent / pyridine

7: n-Bu₄NF, imidazole / tetrahydrofuran

8: DBU / CH₂Cl₂

9: 83 percent / i-Pr₂NEt / CH₂Cl₂

10: 90 percent / DIBAL / diethyl ether / 1.17 h / -78 - 23 °C

11: pyridine, DMAP / dimethylformamide / 3.17 h / 0 - 23 °C

12: AgNO₃, pyridine / dimethylformamide

13: PPTS / methanol; CH₂Cl₂

14: 89 percent / NaH / tetrahydrofuran / 23 °C

15: n-Bu₄NF / tetrahydrofuran / 12 h / 23 °C

16: NaH, n-Bu₄NI / dimethylformamide / 24 h / 23 °C

17: 83 percent / DIBAL / CH₂Cl₂ / 12.5 h / -78 - 23 °C

18: I₂, Ph₃P, imidazole / benzene / 1 h / 23 °C

19: dimethylformamide / 4 h / 55 °C

With pyridine; 1H-imidazole; chromium dichloride; dmap; sodium periodate; osmium(VIII) oxide; N-methyl-2-indolinone; camphor-10-sulfonic acid; tetrabutyl ammonium fluoride; iodine; pyridinium p-toluenesulfonate; tetra-(n-butyl)ammonium iodide; sodium hydride; diisobutylaluminium hydride; silver nitrate; 1,8-diazabicyclo[5.4.0]undec-7-ene; N-ethyl-N,N-diisopropylamine; triphenylphosphine; nickel dichloride; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; water; dimethyl sulfoxide; N,N-dimethyl-formamide; tert-butyl alcohol; benzene;

DOI:10.1021/ja961230+

Reference yield:

(2R,4aR,6R,7R,8R,8aS)-6-Allyl-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxine-7,8-diol (181267-07-2) → [(2R,3R,4S,4aS,6R,7S,8aR)-3,4,7-Tris-benzyloxy-6-(2-methoxy-ethyl)-octahydro-pyrano[3,2-b]pyran-2-yl]-acetonitrile (181267-41-4)

Guidance literature:

Multi-step reaction with 18 steps

1: 90 percent / AgNO₃, pyridine / dimethylformamide / 4 h / 23 °C

2: OsO₄, NMO / 2-methyl-propan-2-ol; tetrahydrofuran; H₂O

3: NaIO₄ / methanol

4: NiCl₂/CrCl₂ / tetrahydrofuran; dimethylsulfoxide / 23 °C

5: 91 percent / pyridine

6: n-Bu₄NF, imidazole / tetrahydrofuran

7: DBU / CH₂Cl₂

8: 83 percent / i-Pr₂NEt / CH₂Cl₂

9: 90 percent / DIBAL / diethyl ether / 1.17 h / -78 - 23 °C

10: pyridine, DMAP / dimethylformamide / 3.17 h / 0 - 23 °C

11: AgNO₃, pyridine / dimethylformamide

12: PPTS / methanol; CH₂Cl₂

13: 89 percent / NaH / tetrahydrofuran / 23 °C

14: n-Bu₄NF / tetrahydrofuran / 12 h / 23 °C

15: NaH, n-Bu₄NI / dimethylformamide / 24 h / 23 °C

16: 83 percent / DIBAL / CH₂Cl₂ / 12.5 h / -78 - 23 °C

17: I₂, Ph₃P, imidazole / benzene / 1 h / 23 °C

18: dimethylformamide / 4 h / 55 °C

With pyridine; 1H-imidazole; chromium dichloride; dmap; sodium periodate; osmium(VIII) oxide; N-methyl-2-indolinone; tetrabutyl ammonium fluoride; iodine; pyridinium p-toluenesulfonate; tetra-(n-butyl)ammonium iodide; sodium hydride; diisobutylaluminium hydride; silver nitrate; 1,8-diazabicyclo[5.4.0]undec-7-ene; N-ethyl-N,N-diisopropylamine; triphenylphosphine; nickel dichloride; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; water; dimethyl sulfoxide; N,N-dimethyl-formamide; tert-butyl alcohol; benzene;

DOI:10.1021/ja961230+

upstream raw materials:

tetra-n-butylammonium cyanide

(2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl)-1-propene

(2R,3R,4R,5S,6R)-2-allyl-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol

(2R,4aR,6R,7R,8R,8aS)-6-Allyl-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxine-7,8-diol

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