methyl (3R,4R,5S)-5-benzyloxy-3-(tert-butyldimethylsilyloxy)-4-(p-methoxybenzyloxy)hept-6-enoate

Base Information

Chemical Name:methyl (3R,4R,5S)-5-benzyloxy-3-(tert-butyldimethylsilyloxy)-4-(p-methoxybenzyloxy)hept-6-enoate
CAS No.:916154-07-9
Molecular Formula:C₂₉H₄₂O₆Si
Molecular Weight:514.734
Hs Code.:

Synonyms:methyl (3R,4R,5S)-5-benzyloxy-3-(tert-butyldimethylsilyloxy)-4-(p-methoxybenzyloxy)hept-6-enoate

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Chemical Property of methyl (3R,4R,5S)-5-benzyloxy-3-(tert-butyldimethylsilyloxy)-4-(p-methoxybenzyloxy)hept-6-enoate

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Technology Process of methyl (3R,4R,5S)-5-benzyloxy-3-(tert-butyldimethylsilyloxy)-4-(p-methoxybenzyloxy)hept-6-enoate

There total 7 articles about methyl (3R,4R,5S)-5-benzyloxy-3-(tert-butyldimethylsilyloxy)-4-(p-methoxybenzyloxy)hept-6-enoate 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: 75.0%

: 916154-06-8
methyl (3R,4R,5S)-3-(tert-butyldimethylsilyloxy)-5-hydroxy-4-(p-methoxybenzyloxy)hept-6-enoate

: 81927-55-1
O-benzyl 2,2,2-trichloroacetimidate

: 916154-07-9
methyl (3R,4R,5S)-5-benzyloxy-3-(tert-butyldimethylsilyloxy)-4-(p-methoxybenzyloxy)hept-6-enoate

Guidance literature:: With trimethylsilyl trifluoromethanesulfonate; In dichloromethane; for 3h;
DOI:10.1021/jo0615504

Reference yield:

: 916154-05-7
(2R,3R,4R)-4-(tert-butyldimethylsilyloxy)-3-(p-methoxybenzyloxy)-2-vinyl-2,3-dihydro-2H-pyran

: 916154-07-9
methyl (3R,4R,5S)-5-benzyloxy-3-(tert-butyldimethylsilyloxy)-4-(p-methoxybenzyloxy)hept-6-enoate

Guidance literature:: Multi-step reaction with 3 steps

1: 74 percent / pyridinium chlorochromate; silica gel / CH₂Cl₂ / 6 h / 45 °C

2: 83 percent / methanol / 3 h / 20 °C / pH 9 - 10

3: 75 percent / trimethylsilyl trifluoromethanesulfonate / CH₂Cl₂ / 3 h

With trimethylsilyl trifluoromethanesulfonate; silica gel; pyridinium chlorochromate; In methanol; dichloromethane;
DOI:10.1021/jo0615504

Reference yield:

: 916154-04-6
((2R,3R,4R)-4-((tert-butyldimethylsilyl)oxy)-3-((4-methoxybenzyl)oxy)-3,4-dihydro-2H-pyran-2-yl)methanol

: 916154-07-9
methyl (3R,4R,5S)-5-benzyloxy-3-(tert-butyldimethylsilyloxy)-4-(p-methoxybenzyloxy)hept-6-enoate

Guidance literature:: Multi-step reaction with 4 steps

1.1: oxalyl chloride; triethylamine; DMSO / CH₂Cl₂ / 0.5 h / 20 °C

1.2: 75 percent / n-BuLi / CH₂Cl₂; hexane; tetrahydrofuran / 2 h / 20 °C

2.1: 74 percent / pyridinium chlorochromate; silica gel / CH₂Cl₂ / 6 h / 45 °C

3.1: 83 percent / methanol / 3 h / 20 °C / pH 9 - 10

4.1: 75 percent / trimethylsilyl trifluoromethanesulfonate / CH₂Cl₂ / 3 h

With oxalyl dichloride; trimethylsilyl trifluoromethanesulfonate; silica gel; dimethyl sulfoxide; triethylamine; pyridinium chlorochromate; In methanol; dichloromethane; 1.1: Swern oxidation / 1.2: Wittig reaction;
DOI:10.1021/jo0615504