(4S,5S,8S,Z)-methyl 4-(benzyloxy)-5-(tert-butyldimethylsilyloxy)-8-(methoxymethoxy)dodec-2-en-6-ynoate

Base Information

Chemical Name:(4S,5S,8S,Z)-methyl 4-(benzyloxy)-5-(tert-butyldimethylsilyloxy)-8-(methoxymethoxy)dodec-2-en-6-ynoate
CAS No.:1422040-29-6
Molecular Formula:C₂₈H₄₄O₆Si
Molecular Weight:504.739
Hs Code.:

Synonyms:(4S,5S,8S,Z)-methyl 4-(benzyloxy)-5-(tert-butyldimethylsilyloxy)-8-(methoxymethoxy)dodec-2-en-6-ynoate

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Chemical Property of (4S,5S,8S,Z)-methyl 4-(benzyloxy)-5-(tert-butyldimethylsilyloxy)-8-(methoxymethoxy)dodec-2-en-6-ynoate

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Technology Process of (4S,5S,8S,Z)-methyl 4-(benzyloxy)-5-(tert-butyldimethylsilyloxy)-8-(methoxymethoxy)dodec-2-en-6-ynoate

There total 6 articles about (4S,5S,8S,Z)-methyl 4-(benzyloxy)-5-(tert-butyldimethylsilyloxy)-8-(methoxymethoxy)dodec-2-en-6-ynoate 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:

: C₂₆H₄₂O₅Si

: 88738-78-7
bis-(2,2,2-trifluoroethyl)(methoxycarbonylmethyl)phosphonate

: 1422040-29-6
(4S,5S,8S,Z)-methyl 4-(benzyloxy)-5-(tert-butyldimethylsilyloxy)-8-(methoxymethoxy)dodec-2-en-6-ynoate

Guidance literature:: bis-(2,2,2-trifluoroethyl)(methoxycarbonylmethyl)phosphonate; With sodium hydride; In tetrahydrofuran; at 0 ℃; for 0.5h; Inert atmosphere;

C₂₆H₄₂O₅Si; In tetrahydrofuran; at -78 ℃; for 0.666667h; Inert atmosphere;
DOI:10.1016/j.tetlet.2012.12.039

Reference yield:

: 1422040-24-1
(3S,4S,7S)-3-(benzyloxy)-7-(methoxymethoxy)undec-1-en-5-yn-4-ol

: 1422040-29-6
(4S,5S,8S,Z)-methyl 4-(benzyloxy)-5-(tert-butyldimethylsilyloxy)-8-(methoxymethoxy)dodec-2-en-6-ynoate

Guidance literature:: Multi-step reaction with 4 steps

1.1: 2,6-dimethylpyridine / dichloromethane / 1 h

2.1: 4-methylmorpholine N-oxide; osmium(VIII) oxide / toluene; acetone; water / 24 h / 20 °C

3.1: sodium periodate / tetrahydrofuran; water / 0 °C

4.1: sodium hydride / tetrahydrofuran / 0.5 h / 0 °C / Inert atmosphere

4.2: 0.67 h / -78 °C / Inert atmosphere

With 2,6-dimethylpyridine; sodium periodate; osmium(VIII) oxide; sodium hydride; 4-methylmorpholine N-oxide; In tetrahydrofuran; dichloromethane; water; acetone; toluene; 4.2: |Still-Gennary Z-Olefination;
DOI:10.1016/j.tetlet.2012.12.039

Reference yield:

: 1422040-28-5
(5S,8S)-8-((S)-1-(benzyloxy)allyl)-5-butyl-10,10,11,11-tetramethyl-2,4,9-trioxa-10-siladodec-6-yne

: 1422040-29-6
(4S,5S,8S,Z)-methyl 4-(benzyloxy)-5-(tert-butyldimethylsilyloxy)-8-(methoxymethoxy)dodec-2-en-6-ynoate

Guidance literature:: Multi-step reaction with 3 steps

1.1: 4-methylmorpholine N-oxide; osmium(VIII) oxide / toluene; acetone; water / 24 h / 20 °C

2.1: sodium periodate / tetrahydrofuran; water / 0 °C

3.1: sodium hydride / tetrahydrofuran / 0.5 h / 0 °C / Inert atmosphere

3.2: 0.67 h / -78 °C / Inert atmosphere

With sodium periodate; osmium(VIII) oxide; sodium hydride; 4-methylmorpholine N-oxide; In tetrahydrofuran; water; acetone; toluene; 3.2: |Still-Gennary Z-Olefination;
DOI:10.1016/j.tetlet.2012.12.039