2-{(2R,3S,4aR,6S,7S,8R,8aR)-7,8-Bis-benzyloxy-3-(tert-butyl-dimethyl-silanyloxy)-6-[2-(4-methoxy-benzyloxy)-ethyl]-octahydro-pyrano[3,2-b]pyran-2-yl}-ethanol

Base Information

Chemical Name:2-{(2R,3S,4aR,6S,7S,8R,8aR)-7,8-Bis-benzyloxy-3-(tert-butyl-dimethyl-silanyloxy)-6-[2-(4-methoxy-benzyloxy)-ethyl]-octahydro-pyrano[3,2-b]pyran-2-yl}-ethanol
CAS No.:199792-26-2
Molecular Formula:C₄₀H₅₆O₈Si
Molecular Weight:692.965
Hs Code.:

2-{(2R,3S,4aR,6S,7S,8R,8aR)-7,8-Bis-benzyloxy-3-(tert-butyl-dimethyl-silanyloxy)-6-[2-(4-methoxy-benzyloxy)-ethyl]-octahydro-pyrano[3,2-b]pyran-2-yl}-ethanol

Synonyms:2-{(2R,3S,4aR,6S,7S,8R,8aR)-7,8-Bis-benzyloxy-3-(tert-butyl-dimethyl-silanyloxy)-6-[2-(4-methoxy-benzyloxy)-ethyl]-octahydro-pyrano[3,2-b]pyran-2-yl}-ethanol

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Chemical Property of 2-{(2R,3S,4aR,6S,7S,8R,8aR)-7,8-Bis-benzyloxy-3-(tert-butyl-dimethyl-silanyloxy)-6-[2-(4-methoxy-benzyloxy)-ethyl]-octahydro-pyrano[3,2-b]pyran-2-yl}-ethanol

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Technology Process of 2-{(2R,3S,4aR,6S,7S,8R,8aR)-7,8-Bis-benzyloxy-3-(tert-butyl-dimethyl-silanyloxy)-6-[2-(4-methoxy-benzyloxy)-ethyl]-octahydro-pyrano[3,2-b]pyran-2-yl}-ethanol

There total 20 articles about 2-{(2R,3S,4aR,6S,7S,8R,8aR)-7,8-Bis-benzyloxy-3-(tert-butyl-dimethyl-silanyloxy)-6-[2-(4-methoxy-benzyloxy)-ethyl]-octahydro-pyrano[3,2-b]pyran-2-yl}-ethanol 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: 100.0%

: 199792-25-1
{(2R,3S,4aR,6S,7S,8R,8aR)-7,8-Bis-benzyloxy-3-(tert-butyl-dimethyl-silanyloxy)-6-[2-(4-methoxy-benzyloxy)-ethyl]-octahydro-pyrano[3,2-b]pyran-2-yl}-acetic acid methyl ester

: 199792-26-2
2-{(2R,3S,4aR,6S,7S,8R,8aR)-7,8-Bis-benzyloxy-3-(tert-butyl-dimethyl-silanyloxy)-6-[2-(4-methoxy-benzyloxy)-ethyl]-octahydro-pyrano[3,2-b]pyran-2-yl}-ethanol

Guidance literature:: With lithium aluminium tetrahydride; In diethyl ether; at -5 ℃; for 0.5h;
DOI:10.1016/S0040-4020(97)10254-X

Reference yield:

: 50-99-7
D-glucose

: 199792-26-2
2-{(2R,3S,4aR,6S,7S,8R,8aR)-7,8-Bis-benzyloxy-3-(tert-butyl-dimethyl-silanyloxy)-6-[2-(4-methoxy-benzyloxy)-ethyl]-octahydro-pyrano[3,2-b]pyran-2-yl}-ethanol

Guidance literature:: Multi-step reaction with 19 steps

1: TfOH / 48 h / 80 °C

2: PTS*H₂O / dimethylformamide / 4 h / 50 °C

3: 62 percent / NaH / tetrahydrofuran; dimethylformamide / 5 h / Ambient temperature

4: 1.) (Ph₃P)3RhCl, i-Pr₂NEt; 2.) HgCl₂, HgO / 1.) EtOH, reflux, 4 h; 2.) acetone, H₂O, RT, 1 h

5: 99 percent / benzene / 24 h / Heating

6: 94 percent / NaH / tetrahydrofuran / 16 h / Ambient temperature

7: 98 percent / LiAlH₄ / diethyl ether; tetrahydrofuran / 0.5 h / 0 °C

8: KH, TBAI / tetrahydrofuran / 3 h / Ambient temperature

9: 95 percent / DIBAL / CH₂Cl₂ / 1 h / 0 °C

10: NEt₃, DMAP / CH₂Cl₂ / 6 h / Ambient temperature

11: 99 percent / dimethylsulfoxide / 7 h / 50 °C

12: 95 percent / DIBAL / CH₂Cl₂ / 0.5 h / -78 °C

13: 98 percent / LDA / tetrahydrofuran / 1 h / -78 °C

14: 97 percent / 2,6-lutidine / CH₂Cl₂ / 0.25 h / Ambient temperature

15: 99 percent / H₂ / Lindlar catalyst / benzene; methanol / 168 h / Ambient temperature

16: 22 percent / DDQ / CH₂Cl₂; H₂O / 0.5 h / Ambient temperature

17: 1.) NaH; 2.) t-BuOK / 1.) THF, -40 deg C to RT, 2 h; 2.) MeOH, RT, 18 h

18: 75 percent / TfOH / diethyl ether / 0.17 h / Ambient temperature

19: LiAlH₄ / diethyl ether / 0.5 h / -10 °C

With 2,6-dimethylpyridine; dmap; Wilkinson's catalyst; lithium aluminium tetrahydride; trifluorormethanesulfonic acid; PTS*H₂O; potassium tert-butylate; hydrogen; tetra-(n-butyl)ammonium iodide; potassium hydride; sodium hydride; diisobutylaluminium hydride; triethylamine; N-ethyl-N,N-diisopropylamine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; mercury dichloride; mercury(II) oxide; lithium diisopropyl amide; Lindlar's catalyst; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; water; dimethyl sulfoxide; N,N-dimethyl-formamide; benzene;
DOI:10.1016/S0040-4039(97)10107-1

Reference yield:

: 48149-74-2,821794-45-0
allyl D-glucopyranoside

: 199792-26-2
2-{(2R,3S,4aR,6S,7S,8R,8aR)-7,8-Bis-benzyloxy-3-(tert-butyl-dimethyl-silanyloxy)-6-[2-(4-methoxy-benzyloxy)-ethyl]-octahydro-pyrano[3,2-b]pyran-2-yl}-ethanol

Guidance literature:: Multi-step reaction with 18 steps

1: PTS*H₂O / dimethylformamide / 4 h / 50 °C

2: 62 percent / NaH / tetrahydrofuran; dimethylformamide / 5 h / Ambient temperature

3: 1.) (Ph₃P)3RhCl, i-Pr₂NEt; 2.) HgCl₂, HgO / 1.) EtOH, reflux, 4 h; 2.) acetone, H₂O, RT, 1 h

4: 99 percent / benzene / 24 h / Heating

5: 94 percent / NaH / tetrahydrofuran / 16 h / Ambient temperature

6: 98 percent / LiAlH₄ / diethyl ether; tetrahydrofuran / 0.5 h / 0 °C

7: KH, TBAI / tetrahydrofuran / 3 h / Ambient temperature

8: 95 percent / DIBAL / CH₂Cl₂ / 1 h / 0 °C

9: NEt₃, DMAP / CH₂Cl₂ / 6 h / Ambient temperature

10: 99 percent / dimethylsulfoxide / 7 h / 50 °C

11: 95 percent / DIBAL / CH₂Cl₂ / 0.5 h / -78 °C

12: 98 percent / LDA / tetrahydrofuran / 1 h / -78 °C

13: 97 percent / 2,6-lutidine / CH₂Cl₂ / 0.25 h / Ambient temperature

14: 99 percent / H₂ / Lindlar catalyst / benzene; methanol / 168 h / Ambient temperature

15: 22 percent / DDQ / CH₂Cl₂; H₂O / 0.5 h / Ambient temperature

16: 1.) NaH; 2.) t-BuOK / 1.) THF, -40 deg C to RT, 2 h; 2.) MeOH, RT, 18 h

17: 75 percent / TfOH / diethyl ether / 0.17 h / Ambient temperature

18: LiAlH₄ / diethyl ether / 0.5 h / -10 °C

With 2,6-dimethylpyridine; dmap; Wilkinson's catalyst; lithium aluminium tetrahydride; trifluorormethanesulfonic acid; PTS*H₂O; potassium tert-butylate; hydrogen; tetra-(n-butyl)ammonium iodide; potassium hydride; sodium hydride; diisobutylaluminium hydride; triethylamine; N-ethyl-N,N-diisopropylamine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; mercury dichloride; mercury(II) oxide; lithium diisopropyl amide; Lindlar's catalyst; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; water; dimethyl sulfoxide; N,N-dimethyl-formamide; benzene;
DOI:10.1016/S0040-4039(97)10107-1