(2S,3S,4S,5S,6S)-1-benzyloxy-2,4,6-trimethyl-8-((2S,4R,6S)-2-methyl-4-methoxytetrahydropyran-6-yl)-3,5-di-tert-butylsilylenedioxyoctane

Base Information

Chemical Name:(2S,3S,4S,5S,6S)-1-benzyloxy-2,4,6-trimethyl-8-((2S,4R,6S)-2-methyl-4-methoxytetrahydropyran-6-yl)-3,5-di-tert-butylsilylenedioxyoctane
CAS No.:142144-31-8
Molecular Formula:C₃₃H₅₈O₅Si
Molecular Weight:562.906
Hs Code.:

Synonyms:(2S,3S,4S,5S,6S)-1-benzyloxy-2,4,6-trimethyl-8-((2S,4R,6S)-2-methyl-4-methoxytetrahydropyran-6-yl)-3,5-di-tert-butylsilylenedioxyoctane

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Chemical Property of (2S,3S,4S,5S,6S)-1-benzyloxy-2,4,6-trimethyl-8-((2S,4R,6S)-2-methyl-4-methoxytetrahydropyran-6-yl)-3,5-di-tert-butylsilylenedioxyoctane

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Technology Process of (2S,3S,4S,5S,6S)-1-benzyloxy-2,4,6-trimethyl-8-((2S,4R,6S)-2-methyl-4-methoxytetrahydropyran-6-yl)-3,5-di-tert-butylsilylenedioxyoctane

There total 10 articles about (2S,3S,4S,5S,6S)-1-benzyloxy-2,4,6-trimethyl-8-((2S,4R,6S)-2-methyl-4-methoxytetrahydropyran-6-yl)-3,5-di-tert-butylsilylenedioxyoctane 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: 96.0%

: Imidazole-1-carbothioic acid O-[(1S,2S)-2-[(4S,5R,6S)-6-((S)-2-benzyloxy-1-methyl-ethyl)-2,2-di-tert-butyl-5-methyl-[1,3,2]dioxasilinan-4-yl]-1-((2R,4R,6S)-4-methoxy-6-methyl-tetrahydro-pyran-2-ylmethyl)-propyl] ester

: 142144-31-8
(2S,3S,4S,5S,6S)-1-benzyloxy-2,4,6-trimethyl-8-((2S,4R,6S)-2-methyl-4-methoxytetrahydropyran-6-yl)-3,5-di-tert-butylsilylenedioxyoctane

Guidance literature:: With tri-n-butyl-tin hydride; In toluene; for 0.5h; Heating;
DOI:10.1016/0040-4020(95)00546-K

Reference yield:

: 237056-36-9
(2S,4R,6RS)-2-methyl-4,6-dimethoxytetrahydropyran

: 142144-31-8
(2S,3S,4S,5S,6S)-1-benzyloxy-2,4,6-trimethyl-8-((2S,4R,6S)-2-methyl-4-methoxytetrahydropyran-6-yl)-3,5-di-tert-butylsilylenedioxyoctane

Guidance literature:: Multi-step reaction with 8 steps

1: 96 percent / Me₃SiOTf / acetonitrile / 0.03 h / -20 °C

2: 1) O₃, NaHCO₃(s), 2) Me₂S / 1) CH₂Cl₂/MeOH, -78 deg C, 10 min, 2) 20 deg C,

3: benzene / 18 h / Heating

5: 84 percent / Me₄NBH(OAc)3 / acetic acid; acetonitrile / 19 h / -20 °C

6: 86 percent / 2,6-lutidine / CH₂Cl₂ / 17 h / 20 °C

7: 1) thexylborane, 2) H₂O₂/NaOH / 1) THF, 20 deg C, 3 h, 2) 1 h

8: 2) nBu₃SnH / 1) THF, 60 deg C, 16 h, 2) toluene, reflux, 50 min

With 2,6-dimethylpyridine; sodium hydroxide; dimethylsulfide; thexylborane; dihydrogen peroxide; tri-n-butyl-tin hydride; sodium hydrogencarbonate; ozone; tetramethylammonium triacetoxyborohydride; trimethylsilyl trifluoromethanesulfonate; In dichloromethane; acetic acid; acetonitrile; benzene;
DOI:10.1016/S0040-4039(00)78876-9

Reference yield:

: 116546-78-2
(S)-1-benzyloxy-2-methylpentan-3-one

: 142144-31-8
(2S,3S,4S,5S,6S)-1-benzyloxy-2,4,6-trimethyl-8-((2S,4R,6S)-2-methyl-4-methoxytetrahydropyran-6-yl)-3,5-di-tert-butylsilylenedioxyoctane

Guidance literature:: Multi-step reaction with 5 steps

2: 84 percent / Me₄NBH(OAc)3 / acetic acid; acetonitrile / 19 h / -20 °C

3: 86 percent / 2,6-lutidine / CH₂Cl₂ / 17 h / 20 °C

4: 1) thexylborane, 2) H₂O₂/NaOH / 1) THF, 20 deg C, 3 h, 2) 1 h

5: 2) nBu₃SnH / 1) THF, 60 deg C, 16 h, 2) toluene, reflux, 50 min

With 2,6-dimethylpyridine; sodium hydroxide; thexylborane; dihydrogen peroxide; tri-n-butyl-tin hydride; tetramethylammonium triacetoxyborohydride; In dichloromethane; acetic acid; acetonitrile;
DOI:10.1016/S0040-4039(00)78876-9