(E)-(3S,4S)-3-(tert-Butyl-dimethyl-silanyloxy)-1-((2R,3R,4S,5R,6S)-3,4,5-tris-benzyloxy-6-methoxy-tetrahydro-pyran-2-yl)-dodec-1-en-5-yn-4-ol

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Chemical Name:(E)-(3S,4S)-3-(tert-Butyl-dimethyl-silanyloxy)-1-((2R,3R,4S,5R,6S)-3,4,5-tris-benzyloxy-6-methoxy-tetrahydro-pyran-2-yl)-dodec-1-en-5-yn-4-ol
CAS No.:168007-62-3
Molecular Formula:C₄₅H₆₂O₇Si
Molecular Weight:743.069
Hs Code.:
Mol file:168007-62-3.mol

Synonyms:(E)-(3S,4S)-3-(tert-Butyl-dimethyl-silanyloxy)-1-((2R,3R,4S,5R,6S)-3,4,5-tris-benzyloxy-6-methoxy-tetrahydro-pyran-2-yl)-dodec-1-en-5-yn-4-ol

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Chemical Property of (E)-(3S,4S)-3-(tert-Butyl-dimethyl-silanyloxy)-1-((2R,3R,4S,5R,6S)-3,4,5-tris-benzyloxy-6-methoxy-tetrahydro-pyran-2-yl)-dodec-1-en-5-yn-4-ol Edit

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Technology Process of (E)-(3S,4S)-3-(tert-Butyl-dimethyl-silanyloxy)-1-((2R,3R,4S,5R,6S)-3,4,5-tris-benzyloxy-6-methoxy-tetrahydro-pyran-2-yl)-dodec-1-en-5-yn-4-ol

There total 2 articles about (E)-(3S,4S)-3-(tert-Butyl-dimethyl-silanyloxy)-1-((2R,3R,4S,5R,6S)-3,4,5-tris-benzyloxy-6-methoxy-tetrahydro-pyran-2-yl)-dodec-1-en-5-yn-4-ol 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:

: 1846-69-1
non-2-ynal

: 18162-48-6
tert-butyldimethylsilyl chloride

: 113421-14-0
methyl (E)-2,3,4-tri-O-benzyl-6,7-dideoxy-α-D-gluco-oct-6-enodialdo-1,5-pyranoside

: 168007-62-3
(E)-(3S,4S)-3-(tert-Butyl-dimethyl-silanyloxy)-1-((2R,3R,4S,5R,6S)-3,4,5-tris-benzyloxy-6-methoxy-tetrahydro-pyran-2-yl)-dodec-1-en-5-yn-4-ol

Guidance literature:: Yield given. Multistep reaction;
DOI:10.1021/jo00114a009

Reference yield:

: 115520-84-8
methyl 2,3,4-tri-O-benzyl-6,7-dideoxy-6(E)-eno-α-D-gluco-oct-1,5-pyranoside

: 168007-62-3
(E)-(3S,4S)-3-(tert-Butyl-dimethyl-silanyloxy)-1-((2R,3R,4S,5R,6S)-3,4,5-tris-benzyloxy-6-methoxy-tetrahydro-pyran-2-yl)-dodec-1-en-5-yn-4-ol

Guidance literature:: Multi-step reaction with 2 steps

1: 1.) oxalyl chloride, DMSO, 2.) Et₃N / 1.) CH₂Cl₂, -78 deg C, 30 min, 2.) -78 deg to 0 deg C, 20 min

2: 1.) CuCN, n-BuLi, Bu₃SnH, 3.) BF₃*OEt₂ / 1.) THF, hexane, -78 deg C, 25 min; 30 min 2.) -78 deg C, 30 min, 3.) CH₂Cl₂, -78 deg C, 1.5 h

With n-butyllithium; oxalyl dichloride; boron trifluoride diethyl etherate; tri-n-butyl-tin hydride; dimethyl sulfoxide; triethylamine;
DOI:10.1021/jo9601627