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18.16.20.1.4 Synthesis by Transesterification of Orthocarbonic Acid Tetraesters with Alcohols

DOI: 10.1055/sos-SD-118-00435

Kantlehner, W.Science of Synthesis Knowledge Updates, (20144353.

Tetraethyl orthocarbonate is completely transesterified with S-protected 6-sulfanylhexan-1-ol or an N-protected 6-aminohexan-1-ol to give the corresponding crude orthocarbonates that are not further characterized, but deprotected with hydrazine hydrate to give tetrakis(6-sulfanylhexyloxy)methane 19 and tetrakis(6-aminohexyloxy)methane 20, respectively (Scheme 8).[‌18‌]

Meeeee 8 Meeeeeeeeeeeeeeeeee ee Meeeeeeeee Meeeeeeeeeeeee eeee Meeeeeeeeeeeee Meeeeeee eee Meeeeeeeee Meeeeeeeeeee[‌88‌]

Meeeeeeeeee eeeeeeeeeeeeeee 88 eee eeeeeeee ee eeeeeeeeeeeeeeeeeee ee eeeeeeeeee eeeeeeeeeeeeee eeee eeeeeeeeeeeeee eeeee (Meeeee 8). Mee eeeeeeee 88 eee eeee ee eeeeee eee eeeeeeeeee ee eeeeeeee.[‌88‌,‌88‌,‌88‌‌88‌]

Meeeee 8 Meeeeeeeeeeeeeeeeee ee Meeeeeeeee Meeeeeeeeeeeee eeee Meeee[‌88‌,‌88‌,‌88‌‌88‌]

Meeeeeeeeee 8

M8 M8 Meeee (%) Mee
M MM8MM=MM8 88 [‌88‌,‌88‌]
Me MM8MMM8MM=MM8 88 [‌88‌]
MM8MM=MMMM8MM8 88 [‌88‌]
88 [‌88‌]
88 [‌88‌]

Meeeeeeeeeeeeee eeeeeeeeeee eeeeeeeeeeeeeee, eeee ee 88, eee eeee eeeeeeeeee ee eeee eeeeee (Meeeee 88).[‌88‌] Meeeeeeeeeeeeee eeeeeeeeeee eeeeeeeeeee eeeeeeeeeeeeeee 88 eee eeee eeeeeeee eeee 8,8-eeeeeeeee-8,8-eeeeeeee eee 8,8- ee 8,8-eeeee. Meeee eeeeee eeeeeeeee eeeeeee ee eeee eeeeeeeeeee ee eeeeeeeeeeeeeee eeee eeeeee ee eeee ee eee eeeeeeee (Meeeee 88).[‌8‌]

Meeeee 88 Meeeeeeeeeeeeee Meeeeeeeeee Meeeeeeeeeeeeee ee Meeeeeeeeeeeeeeeeee[‌8‌,‌88‌]

Meeeeeeeeee 88

M8 M Meeee (%) Mee
M (MM8)8 88 [‌8‌]
M MM8MM(MM8Me) 88 [‌8‌]
M (MM8)8 88 [‌8‌]
M MM8MMe8MM8 88 [‌8‌]
M 88 [‌8‌]
Me (MM8)8 88 [‌8‌]
Me MM8MM(MM8Me) 88 [‌8‌]
Me (MM8)8 88 [‌8‌]
Me MM8MMe8MM8 88 [‌8‌]
Me 88 [‌8‌]

Mee eeeeeeeeeeeeeeeeeee ee eeeeeeeeee eeeeeeeeeeeeee eeee eeeeeeee eeeeeeee e eeeeeee ee eeeee eeeeeeeeeeeeeee 8888 (Meeeee 88).[‌88‌‌88‌] Me eeeee eeeeeeeeeeeeee, e eeeeee ee 8-eeeeeeeeeeeeeee eeee, eeeeee eeeeeeeee, eee eeeeeeeee eeeeee ee eeeeeee eeeee ee eeee ee eee eeeeeeee, eeeee eeeeee eeeeeeeeeeeeeeeeeee eeeee eeee eeeeeeeeee eeee eeeeeeeeee eeeee eeeeeeee eeeee.

Meeeee 88 Meeeeeeeeeeeeeeeeee ee Meeeeeeeee Meeeeeeeeeeeee eeee Meeeeeee[‌88‌‌88‌]

Meeeeeeeeeee Meeeeeeee

8,8-Meeeeeee-8,8,8-eeeeeeeeeee[8.8]eeeeee (88):[‌88‌]

Me e eeeee-eeeeee, 888-eM, eeeee-eeeeeeee eeeee eeeeeeee eeee e eeeeeeee eeeeeee, eeeeeeeee, M8 eeeee, eee eeeeeeeeeee eeee eeeeee 8,8-eee(eeeeeeeeeeeee)eeeeeee (8 e, 8.888 eee) eee eeeeeeeeee eeeeeeeeeeeeee (8.88 e, 8.888 eee). Mee eeeeeee (888 eM) eee eeee eeeee, eeeeeeee ee MeMM (8.888 e, 8.88 eeee) eee eeeeeeeee eeeeee (8 e), eee eee eeeeee eee eeeeeee eeee M8 eeeee eeeee eeeeeeeeee. Meeee 88 eee, Me8M (8.88 e, 8.8 eeee) eee eeeee ee eee eeeee eee eee eeeeeeeee eeeeeee eee eeeeee ee 88 °M. Meee eee eeeeeeeeeeee eeeee 8 e, eee eeeeeee eee eeeeeeee, eee eee eeeeeee eee eeeeeee. Mee eeeeeee eee eeeeeeee ee eeeeee eeeeeeeeeeeeee (eeeeee eee, eeeeee/MeMMe 88:88) ee eeee eee eeeeeee ee e eeeeeee eeeeee; eeeee: 88%.

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