(4R,4aS,6R,7S,8aR)-7-Methoxy-2-[(2R,3S)-3-(4-methoxy-benzyloxy)-tetrahydro-pyran-2-ylmethyl]-6-methoxymethyl-4a-methyl-4,4a,6,7,8,8a-hexahydro-pyrano[3,2-b]pyran-4-ol

Base Information

Chemical Name:(4R,4aS,6R,7S,8aR)-7-Methoxy-2-[(2R,3S)-3-(4-methoxy-benzyloxy)-tetrahydro-pyran-2-ylmethyl]-6-methoxymethyl-4a-methyl-4,4a,6,7,8,8a-hexahydro-pyrano[3,2-b]pyran-4-ol
CAS No.:455958-58-4
Molecular Formula:C₂₆H₃₈O₈
Molecular Weight:478.583
Hs Code.:

(4R,4aS,6R,7S,8aR)-7-Methoxy-2-[(2R,3S)-3-(4-methoxy-benzyloxy)-tetrahydro-pyran-2-ylmethyl]-6-methoxymethyl-4a-methyl-4,4a,6,7,8,8a-hexahydro-pyrano[3,2-b]pyran-4-ol

Synonyms:(4R,4aS,6R,7S,8aR)-7-Methoxy-2-[(2R,3S)-3-(4-methoxy-benzyloxy)-tetrahydro-pyran-2-ylmethyl]-6-methoxymethyl-4a-methyl-4,4a,6,7,8,8a-hexahydro-pyrano[3,2-b]pyran-4-ol

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Chemical Property of (4R,4aS,6R,7S,8aR)-7-Methoxy-2-[(2R,3S)-3-(4-methoxy-benzyloxy)-tetrahydro-pyran-2-ylmethyl]-6-methoxymethyl-4a-methyl-4,4a,6,7,8,8a-hexahydro-pyrano[3,2-b]pyran-4-ol

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Technology Process of (4R,4aS,6R,7S,8aR)-7-Methoxy-2-[(2R,3S)-3-(4-methoxy-benzyloxy)-tetrahydro-pyran-2-ylmethyl]-6-methoxymethyl-4a-methyl-4,4a,6,7,8,8a-hexahydro-pyrano[3,2-b]pyran-4-ol

There total 17 articles about (4R,4aS,6R,7S,8aR)-7-Methoxy-2-[(2R,3S)-3-(4-methoxy-benzyloxy)-tetrahydro-pyran-2-ylmethyl]-6-methoxymethyl-4a-methyl-4,4a,6,7,8,8a-hexahydro-pyrano[3,2-b]pyran-4-ol 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: 94.0%

: 455958-57-3
(4aR,6R,7S,8aR)-7-Methoxy-2-[(2R,3S)-3-(4-methoxy-benzyloxy)-tetrahydro-pyran-2-ylmethyl]-6-methoxymethyl-4a-methyl-6,7,8,8a-tetrahydro-4aH-pyrano[3,2-b]pyran-4-one

: 455958-58-4
(4R,4aS,6R,7S,8aR)-7-Methoxy-2-[(2R,3S)-3-(4-methoxy-benzyloxy)-tetrahydro-pyran-2-ylmethyl]-6-methoxymethyl-4a-methyl-4,4a,6,7,8,8a-hexahydro-pyrano[3,2-b]pyran-4-ol

Guidance literature:: With diisobutylaluminium hydride; In toluene; at -78 ℃; for 0.166667h;
DOI:10.1021/ol026261q

Reference yield:

: 455958-46-0
C₁₈H₂₄O₅

: 455958-58-4
(4R,4aS,6R,7S,8aR)-7-Methoxy-2-[(2R,3S)-3-(4-methoxy-benzyloxy)-tetrahydro-pyran-2-ylmethyl]-6-methoxymethyl-4a-methyl-4,4a,6,7,8,8a-hexahydro-pyrano[3,2-b]pyran-4-ol

Guidance literature:: Multi-step reaction with 12 steps

1.1: 99 percent / H₂ / Pd(OH)2 / ethyl acetate / 20 °C

2.1: NaH / tetrahydrofuran / 20 °C

3.1: CSA; methanol / 20 °C

4.1: 2,6-lutidine / CH₂Cl₂ / 0 °C

5.1: CSA; methanol / 20 °C

6.1: 100 percent / (COCl)2; DMSO; Et₃N / CH₂Cl₂ / -78 °C

7.1: t-butyllithium / tetrahydrofuran; pentane; hexamethylphosphoric acid triamide / 0.17 h / -78 °C

7.2: 76 percent / tetrahydrofuran; pentane; hexamethylphosphoric acid triamide / 0.25 h / -78 °C

8.1: 100 percent / oxalyl chloride; dimethyl sulfoxide; triethylamine / CH₂Cl₂ / -78 - 20 °C

9.1: 92 percent / methanol / 12 h / 20 °C

10.1: 83 percent / tetra-n-butylammonium fluoride / tetrahydrofuran / 6 h / 20 °C

11.1: 76 percent / p-toluenesulfonic acid monohydrate / toluene / 1 h / 60 °C

12.1: 94 percent / DIBAH / toluene / 0.17 h / -78 °C

With 2,6-dimethylpyridine; methanol; oxalyl dichloride; camphor-10-sulfonic acid; tetrabutyl ammonium fluoride; hydrogen; tert.-butyl lithium; sodium hydride; diisobutylaluminium hydride; toluene-4-sulfonic acid; dimethyl sulfoxide; triethylamine; palladium dihydroxide; In tetrahydrofuran; methanol; N,N,N,N,N,N-hexamethylphosphoric triamide; dichloromethane; ethyl acetate; toluene; pentane; 8.1: Swern oxidation / 11.1: hetero-Michael cyclization;
DOI:10.1021/ol026261q

Reference yield:

: C₁₅H₂₀O₅

: 455958-58-4
(4R,4aS,6R,7S,8aR)-7-Methoxy-2-[(2R,3S)-3-(4-methoxy-benzyloxy)-tetrahydro-pyran-2-ylmethyl]-6-methoxymethyl-4a-methyl-4,4a,6,7,8,8a-hexahydro-pyrano[3,2-b]pyran-4-ol

Guidance literature:: Multi-step reaction with 13 steps

1.1: 94 percent / CSA / dimethylformamide / 20 °C

2.1: 99 percent / H₂ / Pd(OH)2 / ethyl acetate / 20 °C

3.1: NaH / tetrahydrofuran / 20 °C

4.1: CSA; methanol / 20 °C

5.1: 2,6-lutidine / CH₂Cl₂ / 0 °C

6.1: CSA; methanol / 20 °C

7.1: 100 percent / (COCl)2; DMSO; Et₃N / CH₂Cl₂ / -78 °C

8.1: t-butyllithium / tetrahydrofuran; pentane; hexamethylphosphoric acid triamide / 0.17 h / -78 °C

8.2: 76 percent / tetrahydrofuran; pentane; hexamethylphosphoric acid triamide / 0.25 h / -78 °C

9.1: 100 percent / oxalyl chloride; dimethyl sulfoxide; triethylamine / CH₂Cl₂ / -78 - 20 °C

10.1: 92 percent / methanol / 12 h / 20 °C

11.1: 83 percent / tetra-n-butylammonium fluoride / tetrahydrofuran / 6 h / 20 °C

12.1: 76 percent / p-toluenesulfonic acid monohydrate / toluene / 1 h / 60 °C

13.1: 94 percent / DIBAH / toluene / 0.17 h / -78 °C

With 2,6-dimethylpyridine; methanol; oxalyl dichloride; camphor-10-sulfonic acid; tetrabutyl ammonium fluoride; hydrogen; tert.-butyl lithium; sodium hydride; diisobutylaluminium hydride; toluene-4-sulfonic acid; dimethyl sulfoxide; triethylamine; palladium dihydroxide; In tetrahydrofuran; methanol; N,N,N,N,N,N-hexamethylphosphoric triamide; dichloromethane; ethyl acetate; N,N-dimethyl-formamide; toluene; pentane; 9.1: Swern oxidation / 12.1: hetero-Michael cyclization;
DOI:10.1021/ol026261q