(2S,3S,4S,5S)-2-[(S)-2,3-Bis-(tert-butyl-dimethyl-silanyloxy)-propyl]-3-methoxy-4-(4-methoxy-benzyloxy)-5-vinyl-tetrahydro-furan

Base Information

Chemical Name:(2S,3S,4S,5S)-2-[(S)-2,3-Bis-(tert-butyl-dimethyl-silanyloxy)-propyl]-3-methoxy-4-(4-methoxy-benzyloxy)-5-vinyl-tetrahydro-furan
CAS No.:808109-92-4
Molecular Formula:C₃₀H₅₄O₆Si₂
Molecular Weight:566.926
Hs Code.:

Synonyms:(2S,3S,4S,5S)-2-[(S)-2,3-Bis-(tert-butyl-dimethyl-silanyloxy)-propyl]-3-methoxy-4-(4-methoxy-benzyloxy)-5-vinyl-tetrahydro-furan

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Chemical Property of (2S,3S,4S,5S)-2-[(S)-2,3-Bis-(tert-butyl-dimethyl-silanyloxy)-propyl]-3-methoxy-4-(4-methoxy-benzyloxy)-5-vinyl-tetrahydro-furan

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Technology Process of (2S,3S,4S,5S)-2-[(S)-2,3-Bis-(tert-butyl-dimethyl-silanyloxy)-propyl]-3-methoxy-4-(4-methoxy-benzyloxy)-5-vinyl-tetrahydro-furan

There total 14 articles about (2S,3S,4S,5S)-2-[(S)-2,3-Bis-(tert-butyl-dimethyl-silanyloxy)-propyl]-3-methoxy-4-(4-methoxy-benzyloxy)-5-vinyl-tetrahydro-furan 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:

: 1779-49-3
Methyltriphenylphosphonium bromide

: (2R,3R,4S,5S)-5-[(S)-2,3-Bis-(tert-butyl-dimethyl-silanyloxy)-propyl]-4-methoxy-3-(4-methoxy-benzyloxy)-tetrahydro-furan-2-carbaldehyde

: 808109-92-4
(2S,3S,4S,5S)-2-[(S)-2,3-Bis-(tert-butyl-dimethyl-silanyloxy)-propyl]-3-methoxy-4-(4-methoxy-benzyloxy)-5-vinyl-tetrahydro-furan

Guidance literature:: With n-butyllithium; dimethyl sulfoxide; In tetrahydrofuran; at 0 - 20 ℃;
DOI:10.1016/j.bmcl.2004.08.068

Reference yield:

: 69739-34-0
t-butyldimethylsiyl triflate

: 808109-92-4
(2S,3S,4S,5S)-2-[(S)-2,3-Bis-(tert-butyl-dimethyl-silanyloxy)-propyl]-3-methoxy-4-(4-methoxy-benzyloxy)-5-vinyl-tetrahydro-furan

Guidance literature:: Multi-step reaction with 4 steps

1: Et₃N / CH₂Cl₂ / 0 °C

2: LAH / diethyl ether / 0 °C

3: (COCl)2; DMSO; Et₃N / CH₂Cl₂ / -78 - 0 °C

4: n-BuLi; DMSO / tetrahydrofuran / 0 - 20 °C

With lithium aluminium tetrahydride; n-butyllithium; oxalyl dichloride; dimethyl sulfoxide; triethylamine; In tetrahydrofuran; diethyl ether; dichloromethane;
DOI:10.1016/j.bmcl.2004.08.068

Reference yield:

: 103763-12-8
5-O-tert-butyldiphenylsilyl-α-L-arabinofuranose

: 808109-92-4
(2S,3S,4S,5S)-2-[(S)-2,3-Bis-(tert-butyl-dimethyl-silanyloxy)-propyl]-3-methoxy-4-(4-methoxy-benzyloxy)-5-vinyl-tetrahydro-furan

Guidance literature:: Multi-step reaction with 13 steps

1: pyridine

2: BF₃*Et₂O / hexane / 0 °C

3: K₂CO₃ / methanol

4: imidazole / CH₂Cl₂ / 20 °C

5: NaH / tetrahydrofuran; dimethylformamide / 0 °C

6: TBAF / tetrahydrofuran / 20 °C

7: pyridine / CH₂Cl₂ / 0 - 20 °C

8: 85 percent / BF₃*Et₂O / CH₂Cl₂ / 0 °C

9: aq. OsO₄; NMO / acetone / 20 °C

10: Et₃N / CH₂Cl₂ / 0 °C

11: LAH / diethyl ether / 0 °C

12: (COCl)2; DMSO; Et₃N / CH₂Cl₂ / -78 - 0 °C

13: n-BuLi; DMSO / tetrahydrofuran / 0 - 20 °C

With pyridine; 1H-imidazole; osmium(VIII) oxide; lithium aluminium tetrahydride; n-butyllithium; N-methyl-2-indolinone; oxalyl dichloride; boron trifluoride diethyl etherate; tetrabutyl ammonium fluoride; sodium hydride; potassium carbonate; dimethyl sulfoxide; triethylamine; In tetrahydrofuran; methanol; diethyl ether; hexane; dichloromethane; N,N-dimethyl-formamide; acetone;
DOI:10.1016/j.bmcl.2004.08.068