(2R,4R,4aS,6R,7R,8aR)-7-Benzyloxy-2-{3-[(2R,3R,4S)-4-benzyloxy-3-(tert-butyl-dimethyl-silanyloxy)-tetrahydro-pyran-2-yl]-prop-1-ynyl}-6-benzyloxymethyl-4-(4-methoxy-benzyloxy)-octahydro-pyrano[3,2-b]pyran-2-ol

Base Information

Chemical Name:(2R,4R,4aS,6R,7R,8aR)-7-Benzyloxy-2-{3-[(2R,3R,4S)-4-benzyloxy-3-(tert-butyl-dimethyl-silanyloxy)-tetrahydro-pyran-2-yl]-prop-1-ynyl}-6-benzyloxymethyl-4-(4-methoxy-benzyloxy)-octahydro-pyrano[3,2-b]pyran-2-ol
CAS No.:1053655-14-3
Molecular Formula:C₅₂H₆₆O₁₀Si
Molecular Weight:879.176
Hs Code.:

(2R,4R,4aS,6R,7R,8aR)-7-Benzyloxy-2-{3-[(2R,3R,4S)-4-benzyloxy-3-(tert-butyl-dimethyl-silanyloxy)-tetrahydro-pyran-2-yl]-prop-1-ynyl}-6-benzyloxymethyl-4-(4-methoxy-benzyloxy)-octahydro-pyrano[3,2-b]pyran-2-ol

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Chemical Property of (2R,4R,4aS,6R,7R,8aR)-7-Benzyloxy-2-{3-[(2R,3R,4S)-4-benzyloxy-3-(tert-butyl-dimethyl-silanyloxy)-tetrahydro-pyran-2-yl]-prop-1-ynyl}-6-benzyloxymethyl-4-(4-methoxy-benzyloxy)-octahydro-pyrano[3,2-b]pyran-2-ol

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Technology Process of (2R,4R,4aS,6R,7R,8aR)-7-Benzyloxy-2-{3-[(2R,3R,4S)-4-benzyloxy-3-(tert-butyl-dimethyl-silanyloxy)-tetrahydro-pyran-2-yl]-prop-1-ynyl}-6-benzyloxymethyl-4-(4-methoxy-benzyloxy)-octahydro-pyrano[3,2-b]pyran-2-ol

There total 27 articles about (2R,4R,4aS,6R,7R,8aR)-7-Benzyloxy-2-{3-[(2R,3R,4S)-4-benzyloxy-3-(tert-butyl-dimethyl-silanyloxy)-tetrahydro-pyran-2-yl]-prop-1-ynyl}-6-benzyloxymethyl-4-(4-methoxy-benzyloxy)-octahydro-pyrano[3,2-b]pyran-2-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:

: 2873-29-2
D-glucal triacetate

: 1053655-14-3
(2R,4R,4aS,6R,7R,8aR)-7-Benzyloxy-2-{3-[(2R,3R,4S)-4-benzyloxy-3-(tert-butyl-dimethyl-silanyloxy)-tetrahydro-pyran-2-yl]-prop-1-ynyl}-6-benzyloxymethyl-4-(4-methoxy-benzyloxy)-octahydro-pyrano[3,2-b]pyran-2-ol

Guidance literature:: Multi-step reaction with 12 steps

1: 100 percent / H₂ / Pd/C / methanol / 20 °C

2: 100 percent / NaoMe / methanol / 20 °C

3: 100 percent / PPTS / dimethylformamide / 20 °C

4: (COCl)2; DMSO; Et₃N / CH₂Cl₂ / -78 - 0 °C

5: L-selectride / tetrahydrofuran / -78 °C

6: NaH / dimethylformamide / 0 - 20 °C

7: p-TsOH / methanol / 20 °C

8: 2,6-lutidine / CH₂Cl₂ / -78 °C

9: n-BuLi / tetrahydrofuran; hexamethylphosphoric acid triamide / -78 °C

10: 100 percent / K₂CO₃ / methanol / 20 °C

11: n-BuLi / tetrahydrofuran; hexamethylphosphoric acid triamide / -78 °C

With 2,6-dimethylpyridine; n-butyllithium; oxalyl dichloride; hydrogen; sodium methylate; pyridinium p-toluenesulfonate; L-Selectride; sodium hydride; potassium carbonate; toluene-4-sulfonic acid; dimethyl sulfoxide; triethylamine; palladium on activated charcoal; In tetrahydrofuran; methanol; N,N,N,N,N,N-hexamethylphosphoric triamide; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1016/S0040-4039(01)01067-X

Reference yield:

: 370886-63-8
((2R,3R,4S)-4-Benzyloxy-2-prop-2-ynyl-tetrahydro-pyran-3-yloxy)-tert-butyl-dimethyl-silane

: 370886-74-1
(4R,4aS,6R,7R,8aR)-7-Benzyloxy-6-benzyloxymethyl-4-(4-methoxy-benzyloxy)-hexahydro-pyrano[3,2-b]pyran-2-one

: 1053655-14-3
(2R,4R,4aS,6R,7R,8aR)-7-Benzyloxy-2-{3-[(2R,3R,4S)-4-benzyloxy-3-(tert-butyl-dimethyl-silanyloxy)-tetrahydro-pyran-2-yl]-prop-1-ynyl}-6-benzyloxymethyl-4-(4-methoxy-benzyloxy)-octahydro-pyrano[3,2-b]pyran-2-ol

Guidance literature:: With n-butyllithium; In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide; at -78 ℃;
DOI:10.1016/S0040-4039(01)01067-X

Reference yield:

: 370887-48-2
(2R,3S,4S)-4-Benzyloxy-2-hydroxymethyl-tetrahydro-pyran-3-ol

: 1053655-14-3
(2R,4R,4aS,6R,7R,8aR)-7-Benzyloxy-2-{3-[(2R,3R,4S)-4-benzyloxy-3-(tert-butyl-dimethyl-silanyloxy)-tetrahydro-pyran-2-yl]-prop-1-ynyl}-6-benzyloxymethyl-4-(4-methoxy-benzyloxy)-octahydro-pyrano[3,2-b]pyran-2-ol

Guidance literature:: Multi-step reaction with 5 steps

1: 2,6-lutidine / CH₂Cl₂ / -78 °C

2: n-BuLi / tetrahydrofuran; hexamethylphosphoric acid triamide / -78 °C

3: 100 percent / K₂CO₃ / methanol / 20 °C

4: n-BuLi / tetrahydrofuran; hexamethylphosphoric acid triamide / -78 °C

With 2,6-dimethylpyridine; n-butyllithium; potassium carbonate; In tetrahydrofuran; methanol; N,N,N,N,N,N-hexamethylphosphoric triamide; dichloromethane;
DOI:10.1016/S0040-4039(01)01067-X