(2R,3E,6S,7S,8R)-1,9-di(tert-butyldiphenylsilyloxy)-6-hydroxymethyl-7-(3,4-dimethoxybenzyloxy)-2,4,8-trimethyl-3-nonen-5-one

Base Information

Chemical Name:(2R,3E,6S,7S,8R)-1,9-di(tert-butyldiphenylsilyloxy)-6-hydroxymethyl-7-(3,4-dimethoxybenzyloxy)-2,4,8-trimethyl-3-nonen-5-one
CAS No.:240821-10-7
Molecular Formula:C₅₄H₇₀O₇Si₂
Molecular Weight:887.317
Hs Code.:

Synonyms:(2R,3E,6S,7S,8R)-1,9-di(tert-butyldiphenylsilyloxy)-6-hydroxymethyl-7-(3,4-dimethoxybenzyloxy)-2,4,8-trimethyl-3-nonen-5-one

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Chemical Property of (2R,3E,6S,7S,8R)-1,9-di(tert-butyldiphenylsilyloxy)-6-hydroxymethyl-7-(3,4-dimethoxybenzyloxy)-2,4,8-trimethyl-3-nonen-5-one

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Technology Process of (2R,3E,6S,7S,8R)-1,9-di(tert-butyldiphenylsilyloxy)-6-hydroxymethyl-7-(3,4-dimethoxybenzyloxy)-2,4,8-trimethyl-3-nonen-5-one

There total 17 articles about (2R,3E,6S,7S,8R)-1,9-di(tert-butyldiphenylsilyloxy)-6-hydroxymethyl-7-(3,4-dimethoxybenzyloxy)-2,4,8-trimethyl-3-nonen-5-one 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: 99.0%

: 240821-06-1
(2R,3E,6S,7S,8R)-6-(tert-butyldimethylsilyloxymethyl)-1,9-di(tert-butyldiphenylsilyloxy)-7-(3,4-dimethoxybenzyloxy)-2,4,8-trimethyl-3-nonen-5-one

: 240821-10-7
(2R,3E,6S,7S,8R)-1,9-di(tert-butyldiphenylsilyloxy)-6-hydroxymethyl-7-(3,4-dimethoxybenzyloxy)-2,4,8-trimethyl-3-nonen-5-one

Guidance literature:: With pyridinium p-toluenesulfonate; In ethanol; at 50 ℃;
DOI:10.1055/s-1999-2730

Reference yield:

: (2R,3E,6S,7S,8R)-6-(tert-butyldimethylsilyloxymethyl)-1,9-di(tert-butyldiphenylsilyloxy)-7-(3,4-dimethoxybenzyloxy)-2,4,8-trimethyl-3-nonen-5-ol

: 240821-10-7
(2R,3E,6S,7S,8R)-1,9-di(tert-butyldiphenylsilyloxy)-6-hydroxymethyl-7-(3,4-dimethoxybenzyloxy)-2,4,8-trimethyl-3-nonen-5-one

Guidance literature:: Multi-step reaction with 2 steps

1: 91 percent / Dess-Martin periodinane; pyridine / CH₂Cl₂ / 1 h / 20 °C

2: 99 percent / PPTS / ethanol / 6 h / 50 - 55 °C

With pyridine; pyridinium p-toluenesulfonate; Dess-Martin periodane; In ethanol; dichloromethane; 1: Oxidation / 2: Hydrolysis;
DOI:10.1248/cpb.47.1288

Reference yield:

: 59276-33-4
veratraldehyde dimethyl acetal

: 240821-10-7
(2R,3E,6S,7S,8R)-1,9-di(tert-butyldiphenylsilyloxy)-6-hydroxymethyl-7-(3,4-dimethoxybenzyloxy)-2,4,8-trimethyl-3-nonen-5-one

Guidance literature:: Multi-step reaction with 8 steps

1: 99 percent / CSA / CH₂Cl₂ / Ambient temperature

2: DIBAH / toluene / -30 °C

3: imidazole / CH₂Cl₂ / 0 °C

4: OsO₄, NMO, H₂O / acetone / Ambient temperature

5: NaIO₄, H₂O / tetrahydrofuran / Ambient temperature

6: 1.) tert-BuLi / 1.) Et₂O, 2.) Et₂O, -78 deg C to -30 deg C

7: 91 percent / Dess-Martin reagent, pyridine / CH₂Cl₂ / 0 °C

8: 99 percent / PPTS / ethanol / 50 °C

With pyridine; 1H-imidazole; sodium periodate; osmium(VIII) oxide; N-methyl-2-indolinone; camphor-10-sulfonic acid; water; tert.-butyl lithium; pyridinium p-toluenesulfonate; diisobutylaluminium hydride; Dess-Martin periodane; In tetrahydrofuran; ethanol; dichloromethane; acetone; toluene;
DOI:10.1055/s-1999-2730