(2R,3R,4S,4aS,6R,7S,8aR)-3,4,7-Tris-benzyloxy-2-methoxymethyl-6-vinyl-octahydro-pyrano[3,2-b]pyran

Base Information

Chemical Name:(2R,3R,4S,4aS,6R,7S,8aR)-3,4,7-Tris-benzyloxy-2-methoxymethyl-6-vinyl-octahydro-pyrano[3,2-b]pyran
CAS No.:181262-96-4
Molecular Formula:C₃₃H₃₈O₆
Molecular Weight:530.661
Hs Code.:

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

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

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

There total 17 articles about (2R,3R,4S,4aS,6R,7S,8aR)-3,4,7-Tris-benzyloxy-2-methoxymethyl-6-vinyl-octahydro-pyrano[3,2-b]pyran 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:

: 100-39-0
benzyl bromide

: (2R,3S,4S,4aR,6R,7S,8aR)-2-Methoxymethyl-6-vinyl-octahydro-pyrano[3,2-b]pyran-3,4,7-triol

: 181262-96-4
(2R,3R,4S,4aS,6R,7S,8aR)-3,4,7-Tris-benzyloxy-2-methoxymethyl-6-vinyl-octahydro-pyrano[3,2-b]pyran

Guidance literature:: With tetra-(n-butyl)ammonium iodide; sodium hydride; In N,N-dimethyl-formamide; at 23 ℃; for 24h; Yield given;
DOI:10.1021/ja961230+

Reference yield:

: 181267-46-9
(2R,3R,4R,5S,6R)-2-Allyl-6-methoxymethyl-tetrahydro-pyran-3,4,5-triol

: 181262-96-4
(2R,3R,4S,4aS,6R,7S,8aR)-3,4,7-Tris-benzyloxy-2-methoxymethyl-6-vinyl-octahydro-pyrano[3,2-b]pyran

Guidance literature:: Multi-step reaction with 15 steps

1: i-Pr₂NEt / CH₂Cl₂ / 23 °C

2: 1.) O₃, 2.) Ph₃P / 1.) CH₂Cl₂, MeOH, -78 deg C

3: 1percent NiCl₂/CrCl₂ / tetrahydrofuran / 23 °C

4: pyridine

5: 67 percent / HF*pyridine / acetonitrile / 4 h / 0 °C

6: 81 percent / DBU / CH₂Cl₂ / 20 h

7: 89 percent / AgNO₃, imidazole / dimethylformamide

8: 95 percent / DIBAL / diethyl ether / 1.17 h / -78 - 23 °C

9: 92 percent / pyridine / 0 °C

10: imidazole / dimethylformamide / 2 h / 23 °C

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

12: 95 percent / I₂, Ph₃P, imidazole / benzene

13: 1.) (PhSe)2, NaBH₄, 2.) NaIO₄, i-Pr₂NH / 1.) EtOH, 23 deg C

14: n-Bu₄NF / tetrahydrofuran

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

With pyridine; 1H-imidazole; chromium dichloride; sodium tetrahydroborate; sodium periodate; diphenyl diselenide; tetrabutyl ammonium fluoride; iodine; tetra-(n-butyl)ammonium iodide; sodium hydride; diisobutylaluminium hydride; pyridine hydrogenfluoride; ozone; silver nitrate; 1,8-diazabicyclo[5.4.0]undec-7-ene; diisopropylamine; N-ethyl-N,N-diisopropylamine; triphenylphosphine; nickel dichloride; In tetrahydrofuran; diethyl ether; dichloromethane; N,N-dimethyl-formamide; acetonitrile; benzene;
DOI:10.1021/ja961230+

Reference yield:

: 181267-44-7
(2R,3S,4R,5R,6R)-2-Allyl-3,4,5-tris-benzyloxy-6-methoxymethyl-tetrahydro-pyran

: 181262-96-4
(2R,3R,4S,4aS,6R,7S,8aR)-3,4,7-Tris-benzyloxy-2-methoxymethyl-6-vinyl-octahydro-pyrano[3,2-b]pyran

Guidance literature:: Multi-step reaction with 16 steps

1: Na, liq. NH₃ / tetrahydrofuran / -78 °C

2: i-Pr₂NEt / CH₂Cl₂ / 23 °C

3: 1.) O₃, 2.) Ph₃P / 1.) CH₂Cl₂, MeOH, -78 deg C

4: 1percent NiCl₂/CrCl₂ / tetrahydrofuran / 23 °C

5: pyridine

6: 67 percent / HF*pyridine / acetonitrile / 4 h / 0 °C

7: 81 percent / DBU / CH₂Cl₂ / 20 h

8: 89 percent / AgNO₃, imidazole / dimethylformamide

9: 95 percent / DIBAL / diethyl ether / 1.17 h / -78 - 23 °C

10: 92 percent / pyridine / 0 °C

11: imidazole / dimethylformamide / 2 h / 23 °C

12: DIBAL / diethyl ether / 1.17 h / -78 - 23 °C

13: 95 percent / I₂, Ph₃P, imidazole / benzene

14: 1.) (PhSe)2, NaBH₄, 2.) NaIO₄, i-Pr₂NH / 1.) EtOH, 23 deg C

15: n-Bu₄NF / tetrahydrofuran

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

With pyridine; 1H-imidazole; chromium dichloride; sodium tetrahydroborate; sodium periodate; diphenyl diselenide; tetrabutyl ammonium fluoride; ammonia; iodine; sodium; tetra-(n-butyl)ammonium iodide; sodium hydride; diisobutylaluminium hydride; pyridine hydrogenfluoride; ozone; silver nitrate; 1,8-diazabicyclo[5.4.0]undec-7-ene; diisopropylamine; N-ethyl-N,N-diisopropylamine; triphenylphosphine; nickel dichloride; In tetrahydrofuran; diethyl ether; dichloromethane; N,N-dimethyl-formamide; acetonitrile; benzene;
DOI:10.1021/ja961230+