[(2S,3R,4R,5S,6S)-5-(tert-Butyl-dimethyl-silanyloxy)-6-[2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-3-(4-methoxy-benzyloxy)-4-methyl-tetrahydro-pyran-2-yl]-methanol

Base Information

Chemical Name:[(2S,3R,4R,5S,6S)-5-(tert-Butyl-dimethyl-silanyloxy)-6-[2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-3-(4-methoxy-benzyloxy)-4-methyl-tetrahydro-pyran-2-yl]-methanol
CAS No.:808109-80-0
Molecular Formula:C₃₉H₅₈O₆Si₂
Molecular Weight:679.057
Hs Code.:

[(2S,3R,4R,5S,6S)-5-(tert-Butyl-dimethyl-silanyloxy)-6-[2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-3-(4-methoxy-benzyloxy)-4-methyl-tetrahydro-pyran-2-yl]-methanol

Synonyms:[(2S,3R,4R,5S,6S)-5-(tert-Butyl-dimethyl-silanyloxy)-6-[2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-3-(4-methoxy-benzyloxy)-4-methyl-tetrahydro-pyran-2-yl]-methanol

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Chemical Property of [(2S,3R,4R,5S,6S)-5-(tert-Butyl-dimethyl-silanyloxy)-6-[2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-3-(4-methoxy-benzyloxy)-4-methyl-tetrahydro-pyran-2-yl]-methanol

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Technology Process of [(2S,3R,4R,5S,6S)-5-(tert-Butyl-dimethyl-silanyloxy)-6-[2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-3-(4-methoxy-benzyloxy)-4-methyl-tetrahydro-pyran-2-yl]-methanol

There total 14 articles about [(2S,3R,4R,5S,6S)-5-(tert-Butyl-dimethyl-silanyloxy)-6-[2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-3-(4-methoxy-benzyloxy)-4-methyl-tetrahydro-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: 59.0%

: 808109-42-4
7-(tert-butyl-dimethyl-silanyloxy)-6-[2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-2-(4-methoxy-phenyl)-8-methyl-hexahydro-pyrano[3,2-d][1,3]dioxine

: 808109-80-0
[(2S,3R,4R,5S,6S)-5-(tert-Butyl-dimethyl-silanyloxy)-6-[2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-3-(4-methoxy-benzyloxy)-4-methyl-tetrahydro-pyran-2-yl]-methanol

Guidance literature:: With diisobutylaluminium hydride; In dichloromethane; at -78 ℃;
DOI:10.1016/j.bmcl.2004.08.068

Reference yield:

: 2186-92-7
p-Anisaldehyde dimethyl acetal

: 808109-80-0
[(2S,3R,4R,5S,6S)-5-(tert-Butyl-dimethyl-silanyloxy)-6-[2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-3-(4-methoxy-benzyloxy)-4-methyl-tetrahydro-pyran-2-yl]-methanol

Guidance literature:: Multi-step reaction with 11 steps

1: 90 percent / p-TsOH / dimethylformamide / 20 °C

2: 71 percent / pyridine / 20 °C

3: 79 percent / NaOMe / methanol / 20 °C

4: 75 percent / diethyl ether / Heating

5: 74 percent / (COCl)2; DMSO; Et₃N / CH₂Cl₂ / -78 - 20 °C

6: 88 percent / LAH / diethyl ether / 0 °C

7: DIEA / CH₂Cl₂ / 0 °C

8: O₃ / CH₂Cl₂ / -78 °C

9: NaBH₄ / ethanol / 20 °C

10: 73 percent / imidazole; DMAP / dimethylformamide / 20 °C

11: 59 percent / DIBAL-H / CH₂Cl₂ / -78 °C

With pyridine; 1H-imidazole; dmap; sodium tetrahydroborate; lithium aluminium tetrahydride; oxalyl dichloride; sodium methylate; diisobutylaluminium hydride; toluene-4-sulfonic acid; ozone; dimethyl sulfoxide; triethylamine; N-ethyl-N,N-diisopropylamine; In methanol; diethyl ether; ethanol; dichloromethane; N,N-dimethyl-formamide; 4: Grignard reaction;
DOI:10.1016/j.bmcl.2004.08.068

Reference yield:

: 188783-40-6
α/β‐L‐glucopyranosyl‐1,2,3,4,5‐pentaacetate

: 808109-80-0
[(2S,3R,4R,5S,6S)-5-(tert-Butyl-dimethyl-silanyloxy)-6-[2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-3-(4-methoxy-benzyloxy)-4-methyl-tetrahydro-pyran-2-yl]-methanol

Guidance literature:: Multi-step reaction with 13 steps

1: 67 percent / BF₃*Et₂O / acetonitrile / 80 °C

2: 84 percent / NaOMe / methanol / 20 °C

3: 90 percent / p-TsOH / dimethylformamide / 20 °C

4: 71 percent / pyridine / 20 °C

5: 79 percent / NaOMe / methanol / 20 °C

6: 75 percent / diethyl ether / Heating

7: 74 percent / (COCl)2; DMSO; Et₃N / CH₂Cl₂ / -78 - 20 °C

8: 88 percent / LAH / diethyl ether / 0 °C

9: DIEA / CH₂Cl₂ / 0 °C

10: O₃ / CH₂Cl₂ / -78 °C

11: NaBH₄ / ethanol / 20 °C

12: 73 percent / imidazole; DMAP / dimethylformamide / 20 °C

13: 59 percent / DIBAL-H / CH₂Cl₂ / -78 °C

With pyridine; 1H-imidazole; dmap; sodium tetrahydroborate; lithium aluminium tetrahydride; oxalyl dichloride; boron trifluoride diethyl etherate; sodium methylate; diisobutylaluminium hydride; toluene-4-sulfonic acid; ozone; dimethyl sulfoxide; triethylamine; N-ethyl-N,N-diisopropylamine; In methanol; diethyl ether; ethanol; dichloromethane; N,N-dimethyl-formamide; acetonitrile; 6: Grignard reaction;
DOI:10.1016/j.bmcl.2004.08.068