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

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Chemical Name:(2S,3R,4R,4aS,6R,7S,8aR)-7-Methoxy-2-[(2R,3S)-3-(4-methoxy-benzyloxy)-tetrahydro-pyran-2-ylmethyl]-6-methoxymethyl-4a-methyl-octahydro-pyrano[3,2-b]pyran-3,4-diol
CAS No.:455958-59-5
Molecular Formula:C₂₆H₄₀O₉
Molecular Weight:496.598
Hs Code.:

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

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

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

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

There total 18 articles about (2S,3R,4R,4aS,6R,7S,8aR)-7-Methoxy-2-[(2R,3S)-3-(4-methoxy-benzyloxy)-tetrahydro-pyran-2-ylmethyl]-6-methoxymethyl-4a-methyl-octahydro-pyrano[3,2-b]pyran-3,4-diol 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: 85.0%

: 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

: 455958-59-5
(2S,3R,4R,4aS,6R,7S,8aR)-7-Methoxy-2-[(2R,3S)-3-(4-methoxy-benzyloxy)-tetrahydro-pyran-2-ylmethyl]-6-methoxymethyl-4a-methyl-octahydro-pyrano[3,2-b]pyran-3,4-diol

Guidance literature:: (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; With borane-THF; In tetrahydrofuran; at 0 ℃; for 1h;

With sodium hydroxide; dihydrogen peroxide; In tetrahydrofuran; water; at 0 ℃; for 1h; Further stages.;
DOI:10.1021/ol026261q

Reference yield:

: C₁₅H₂₀O₅

: 455958-59-5
(2S,3R,4R,4aS,6R,7S,8aR)-7-Methoxy-2-[(2R,3S)-3-(4-methoxy-benzyloxy)-tetrahydro-pyran-2-ylmethyl]-6-methoxymethyl-4a-methyl-octahydro-pyrano[3,2-b]pyran-3,4-diol

Guidance literature:: Multi-step reaction with 14 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

14.1: BH₃*THF / tetrahydrofuran / 1 h / 0 °C

14.2: 85 percent / sodium hydroxide; hydrogen peroxide / tetrahydrofuran; H₂O / 1 h / 0 °C

With 2,6-dimethylpyridine; methanol; borane-THF; 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

Reference yield:

: 455958-46-0
C₁₈H₂₄O₅

: 455958-59-5
(2S,3R,4R,4aS,6R,7S,8aR)-7-Methoxy-2-[(2R,3S)-3-(4-methoxy-benzyloxy)-tetrahydro-pyran-2-ylmethyl]-6-methoxymethyl-4a-methyl-octahydro-pyrano[3,2-b]pyran-3,4-diol

Guidance literature:: Multi-step reaction with 13 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

13.1: BH₃*THF / tetrahydrofuran / 1 h / 0 °C

13.2: 85 percent / sodium hydroxide; hydrogen peroxide / tetrahydrofuran; H₂O / 1 h / 0 °C

With 2,6-dimethylpyridine; methanol; borane-THF; 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