[(2R,3R,4aR,8aS)-3-(4-Methoxy-benzyloxy)-octahydro-pyrano[3,2-b]pyran-2-yl]-methanol

Base Information

Chemical Name:[(2R,3R,4aR,8aS)-3-(4-Methoxy-benzyloxy)-octahydro-pyrano[3,2-b]pyran-2-yl]-methanol
CAS No.:181262-25-9
Molecular Formula:C₁₇H₂₄O₅
Molecular Weight:308.375
Hs Code.:

Synonyms:[(2R,3R,4aR,8aS)-3-(4-Methoxy-benzyloxy)-octahydro-pyrano[3,2-b]pyran-2-yl]-methanol

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Chemical Property of [(2R,3R,4aR,8aS)-3-(4-Methoxy-benzyloxy)-octahydro-pyrano[3,2-b]pyran-2-yl]-methanol

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Technology Process of [(2R,3R,4aR,8aS)-3-(4-Methoxy-benzyloxy)-octahydro-pyrano[3,2-b]pyran-2-yl]-methanol

There total 10 articles about [(2R,3R,4aR,8aS)-3-(4-Methoxy-benzyloxy)-octahydro-pyrano[3,2-b]pyran-2-yl]-methanol 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: 98.0%

: (4aR,8aR,9aR,10aS)-2-(4-Methoxy-phenyl)-octahydro-1,3,8,10-tetraoxa-anthracene

: 181262-25-9
[(2R,3R,4aR,8aS)-3-(4-Methoxy-benzyloxy)-octahydro-pyrano[3,2-b]pyran-2-yl]-methanol

Guidance literature:: With diisobutylaluminium hydride; In dichloromethane; at -78 - 0 ℃; for 1.5h;
DOI:10.1021/ja961230+

Reference yield:

: 82598-84-3
2,3,4,6-tetra-O-benzyl-D-galactonolactone

: 181262-25-9
[(2R,3R,4aR,8aS)-3-(4-Methoxy-benzyloxy)-octahydro-pyrano[3,2-b]pyran-2-yl]-methanol

Guidance literature:: Multi-step reaction with 9 steps

1: diethyl ether / 0.25 h / -78 °C

2: Et₃SiH, BF₃*Et₂O / CH₂Cl₂; acetonitrile / 0.25 h / -20 °C

3: 1.) O₃, 2.) NaBH₄ / 1.) MeOH, CH₂Cl₂

4: 98 percent / Et₃N / CH₂Cl₂ / 0.25 h / 0 °C

5: 100 percent / H₂ / Pd(OH)2/C / methanol / 4 h / 23 °C

6: 74 percent / NaH / dimethylformamide / 12 h / 23 °C

7: 97 percent / p-TsOH / dimethylformamide / 12 h / 23 °C

8: 1.) NaH, CS₂, MeI, 2.) n-Bu₃SnH, AIBN / 1.) THF, 23 deg C, 30 min, 2.) toluene, 110 deg C, 1 h

9: 98 percent / DIBAL / CH₂Cl₂ / 1.5 h / -78 - 0 °C

With triethylsilane; carbon disulfide; sodium tetrahydroborate; 2,2'-azobis(isobutyronitrile); boron trifluoride diethyl etherate; hydrogen; tri-n-butyl-tin hydride; sodium hydride; diisobutylaluminium hydride; toluene-4-sulfonic acid; ozone; triethylamine; methyl iodide; palladium dihydroxide; In methanol; diethyl ether; dichloromethane; N,N-dimethyl-formamide; acetonitrile;
DOI:10.1021/ja961230+

Reference yield:

: 181262-24-8
1-(2',3',4',6'-tetra-O-benzyl-β-D-galactopyranosyl)-3-butene

: 181262-25-9
[(2R,3R,4aR,8aS)-3-(4-Methoxy-benzyloxy)-octahydro-pyrano[3,2-b]pyran-2-yl]-methanol

Guidance literature:: Multi-step reaction with 7 steps

1: 1.) O₃, 2.) NaBH₄ / 1.) MeOH, CH₂Cl₂

2: 98 percent / Et₃N / CH₂Cl₂ / 0.25 h / 0 °C

3: 100 percent / H₂ / Pd(OH)2/C / methanol / 4 h / 23 °C

4: 74 percent / NaH / dimethylformamide / 12 h / 23 °C

5: 97 percent / p-TsOH / dimethylformamide / 12 h / 23 °C

6: 1.) NaH, CS₂, MeI, 2.) n-Bu₃SnH, AIBN / 1.) THF, 23 deg C, 30 min, 2.) toluene, 110 deg C, 1 h

7: 98 percent / DIBAL / CH₂Cl₂ / 1.5 h / -78 - 0 °C

With carbon disulfide; sodium tetrahydroborate; 2,2'-azobis(isobutyronitrile); hydrogen; tri-n-butyl-tin hydride; sodium hydride; diisobutylaluminium hydride; toluene-4-sulfonic acid; ozone; triethylamine; methyl iodide; palladium dihydroxide; In methanol; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1021/ja961230+