2-{(2R,4S,5S,6R,7S)-2-tert-butyldiphenylsilyloxymethyl-7-methoxymethoxymethyl-4,7-dimethyl-1-oxaspiro[4.4]non-6-yl}ethyl pivalate

Base Information

Chemical Name:2-{(2R,4S,5S,6R,7S)-2-tert-butyldiphenylsilyloxymethyl-7-methoxymethoxymethyl-4,7-dimethyl-1-oxaspiro[4.4]non-6-yl}ethyl pivalate
CAS No.:1344673-83-1
Molecular Formula:C₃₇H₅₆O₆Si
Molecular Weight:624.934
Hs Code.:

Synonyms:2-{(2R,4S,5S,6R,7S)-2-tert-butyldiphenylsilyloxymethyl-7-methoxymethoxymethyl-4,7-dimethyl-1-oxaspiro[4.4]non-6-yl}ethyl pivalate

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Chemical Property of 2-{(2R,4S,5S,6R,7S)-2-tert-butyldiphenylsilyloxymethyl-7-methoxymethoxymethyl-4,7-dimethyl-1-oxaspiro[4.4]non-6-yl}ethyl pivalate

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Technology Process of 2-{(2R,4S,5S,6R,7S)-2-tert-butyldiphenylsilyloxymethyl-7-methoxymethoxymethyl-4,7-dimethyl-1-oxaspiro[4.4]non-6-yl}ethyl pivalate

There total 25 articles about 2-{(2R,4S,5S,6R,7S)-2-tert-butyldiphenylsilyloxymethyl-7-methoxymethoxymethyl-4,7-dimethyl-1-oxaspiro[4.4]non-6-yl}ethyl pivalate 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%

: 890027-63-1
2-[(2R,4S,5S,6R,7S)-2-{[(tert-butyldiphenylsilyl)oxy]methyl}-7-[(methoxymethoxy)methyl]-4,7-dimethyl-1-oxaspiro[4.4]nonan-6-yl]ethan-1-ol

: 3282-30-2
pivaloyl chloride

: 1344673-83-1
2-{(2R,4S,5S,6R,7S)-2-tert-butyldiphenylsilyloxymethyl-7-methoxymethoxymethyl-4,7-dimethyl-1-oxaspiro[4.4]non-6-yl}ethyl pivalate

Guidance literature:: With pyridine; dmap; In dichloromethane; at 20 ℃; Inert atmosphere;
DOI:10.1002/anie.201104447

Reference yield:

: 890027-31-3
(-)-tert-butyl-[(2R,4S,5S,6R,7S)-7-methoxymethoxymethyl-4,7-dimethyl-6-vinyl-1-oxaspiro[4.4]non-2-ylmethoxy]diphenylsilane

: 1344673-83-1
2-{(2R,4S,5S,6R,7S)-2-tert-butyldiphenylsilyloxymethyl-7-methoxymethoxymethyl-4,7-dimethyl-1-oxaspiro[4.4]non-6-yl}ethyl pivalate

Guidance literature:: Multi-step reaction with 2 steps

1.1: 9-bora-bicyclo[3.3.1]nonane / tetrahydrofuran / 0 - 20 °C / Inert atmosphere

1.2: 20 °C / Inert atmosphere

2.1: pyridine; dmap / dichloromethane / 20 °C / Inert atmosphere

With pyridine; dmap; 9-bora-bicyclo[3.3.1]nonane; In tetrahydrofuran; dichloromethane; 1.1: Hydroboration reaction;
DOI:10.1002/anie.201104447

Reference yield:

: 147200-10-0
(3S,5R)-dihydro-5-hydroxymethyl-3-methyl-2(3H)-furanone

: 1344673-83-1
2-{(2R,4S,5S,6R,7S)-2-tert-butyldiphenylsilyloxymethyl-7-methoxymethoxymethyl-4,7-dimethyl-1-oxaspiro[4.4]non-6-yl}ethyl pivalate

Guidance literature:: Multi-step reaction with 5 steps

1.1: 1H-imidazole / dichloromethane / 20 °C / Inert atmosphere

2.1: tert.-butyl lithium / diethyl ether; pentane / 0.25 h / -78 °C / Inert atmosphere

2.2: -78 °C / Inert atmosphere

3.1: titanium(IV) dichlorodiisopropylate / dichloromethane / 5.5 h / -78 - -50 °C / Inert atmosphere

4.1: 9-bora-bicyclo[3.3.1]nonane / tetrahydrofuran / 3 h / 0 - 20 °C / Inert atmosphere

4.2: 3 h / 20 °C

5.1: dmap; pyridine / dichloromethane / 20 °C / Inert atmosphere

With pyridine; 1H-imidazole; dmap; titanium(IV) dichlorodiisopropylate; tert.-butyl lithium; 9-bora-bicyclo[3.3.1]nonane; In tetrahydrofuran; diethyl ether; dichloromethane; pentane; 3.1: |Hosomi-Sakurai Reaction;
DOI:10.1002/chem.201204119