(2S,3S,4S,6S)-4-(tert-Butyl-dimethyl-silanyloxy)-6-((R)-5-iodomethyl-tetrahydro-furan-3-yl)-6-(4-methoxy-benzyloxy)-2-(2-methoxy-ethoxymethoxy)-3-methyl-hexanal

Base Information

Chemical Name:(2S,3S,4S,6S)-4-(tert-Butyl-dimethyl-silanyloxy)-6-((R)-5-iodomethyl-tetrahydro-furan-3-yl)-6-(4-methoxy-benzyloxy)-2-(2-methoxy-ethoxymethoxy)-3-methyl-hexanal
CAS No.:118207-55-9
Molecular Formula:C₃₀H₅₁IO₈Si
Molecular Weight:694.72
Hs Code.:

(2S,3S,4S,6S)-4-(tert-Butyl-dimethyl-silanyloxy)-6-((R)-5-iodomethyl-tetrahydro-furan-3-yl)-6-(4-methoxy-benzyloxy)-2-(2-methoxy-ethoxymethoxy)-3-methyl-hexanal

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Chemical Property of (2S,3S,4S,6S)-4-(tert-Butyl-dimethyl-silanyloxy)-6-((R)-5-iodomethyl-tetrahydro-furan-3-yl)-6-(4-methoxy-benzyloxy)-2-(2-methoxy-ethoxymethoxy)-3-methyl-hexanal

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Technology Process of (2S,3S,4S,6S)-4-(tert-Butyl-dimethyl-silanyloxy)-6-((R)-5-iodomethyl-tetrahydro-furan-3-yl)-6-(4-methoxy-benzyloxy)-2-(2-methoxy-ethoxymethoxy)-3-methyl-hexanal

There total 14 articles about (2S,3S,4S,6S)-4-(tert-Butyl-dimethyl-silanyloxy)-6-((R)-5-iodomethyl-tetrahydro-furan-3-yl)-6-(4-methoxy-benzyloxy)-2-(2-methoxy-ethoxymethoxy)-3-methyl-hexanal 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: 72.0%

: tert-Butyl-[(1S,2S,3R)-1-[(S)-2-((R)-5-iodomethyl-tetrahydro-furan-3-yl)-2-(4-methoxy-benzyloxy)-ethyl]-3-(2-methoxy-ethoxymethoxy)-2-methyl-pent-4-enyloxy]-dimethyl-silane

: 118207-55-9,118245-55-9
(2S,3S,4S,6S)-4-(tert-Butyl-dimethyl-silanyloxy)-6-((R)-5-iodomethyl-tetrahydro-furan-3-yl)-6-(4-methoxy-benzyloxy)-2-(2-methoxy-ethoxymethoxy)-3-methyl-hexanal

Guidance literature:: With 2,3-dimercapto-succinic acid; ozone;
DOI:10.1021/jo00262a008

Reference yield:

: 118207-58-2
5-(4-methoxybenzyloxy)-3-oxopentanoic acid methyl ester

: 118207-55-9,118245-55-9
(2S,3S,4S,6S)-4-(tert-Butyl-dimethyl-silanyloxy)-6-((R)-5-iodomethyl-tetrahydro-furan-3-yl)-6-(4-methoxy-benzyloxy)-2-(2-methoxy-ethoxymethoxy)-3-methyl-hexanal

Guidance literature:: Multi-step reaction with 13 steps

1: 90 percent / H₂, Et₃N / 1percent Ru₂Cl₄<(S)-binap>2

2: 1.) LDA / 1.) THF, Et₂O, HMPA

3: 86 percent / LiAlH₄

4: 4,5-dichloro-3,6-dioxo-1,4-cyclohexadiene-1,2-dicarbonitrile (DDQ)

5: 76 percent / NaHCO₃, I₂

6: 75 percent / diisobutylaluminum hydride (DIBAL-H)

7: 94 percent / Dess-Martin periodinane reagent

8: 60 percent / SnCl₄ / -78 °C

9: 95 percent

10: 1.) O₃, 2.) PPh₃

11: CH₂Cl₂

12: 86 percent / (i-Pr)2NEt

13: 72 percent / O₃, DMS

With lithium aluminium tetrahydride; 2,3-dimercapto-succinic acid; hydrogen; iodine; tin(IV) chloride; diisobutylaluminium hydride; sodium hydrogencarbonate; Dess-Martin periodane; ozone; triethylamine; N-ethyl-N,N-diisopropylamine; triphenylphosphine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; lithium diisopropyl amide; Ru₂Cl₄((S)-BINAP)2; In dichloromethane;
DOI:10.1021/jo00262a008

Reference yield:

: 69739-34-0
t-butyldimethylsiyl triflate

: 118207-55-9,118245-55-9
(2S,3S,4S,6S)-4-(tert-Butyl-dimethyl-silanyloxy)-6-((R)-5-iodomethyl-tetrahydro-furan-3-yl)-6-(4-methoxy-benzyloxy)-2-(2-methoxy-ethoxymethoxy)-3-methyl-hexanal

Guidance literature:: Multi-step reaction with 5 steps

1: 95 percent

2: 1.) O₃, 2.) PPh₃

3: CH₂Cl₂

4: 86 percent / (i-Pr)2NEt

5: 72 percent / O₃, DMS

With 2,3-dimercapto-succinic acid; ozone; N-ethyl-N,N-diisopropylamine; triphenylphosphine; In dichloromethane;
DOI:10.1021/jo00262a008