6-O-(tert-butyldiphenylsilyl)-7-iodo-1-O-(triphenylmethyl)-2(E),4(Z)-heptadiene-1,6(S)-diol

Base Information

Chemical Name:6-O-(tert-butyldiphenylsilyl)-7-iodo-1-O-(triphenylmethyl)-2(E),4(Z)-heptadiene-1,6(S)-diol
CAS No.:111670-27-0
Molecular Formula:C₄₂H₄₃IO₂Si
Molecular Weight:734.792
Hs Code.:

Synonyms:6-O-(tert-butyldiphenylsilyl)-7-iodo-1-O-(triphenylmethyl)-2(E),4(Z)-heptadiene-1,6(S)-diol

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Chemical Property of 6-O-(tert-butyldiphenylsilyl)-7-iodo-1-O-(triphenylmethyl)-2(E),4(Z)-heptadiene-1,6(S)-diol

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Technology Process of 6-O-(tert-butyldiphenylsilyl)-7-iodo-1-O-(triphenylmethyl)-2(E),4(Z)-heptadiene-1,6(S)-diol

There total 12 articles about 6-O-(tert-butyldiphenylsilyl)-7-iodo-1-O-(triphenylmethyl)-2(E),4(Z)-heptadiene-1,6(S)-diol 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: 83.0%

: 111670-26-9
2-O-(tert-butyldiphenylsilyl)-1-O-<(2,4,6-triisopropylphenyl)sulfonyl>-7-O-(triphenylmethyl)-3(Z),5(E)-heptadiene-1,2(S),7-triol

: 111670-27-0
6-O-(tert-butyldiphenylsilyl)-7-iodo-1-O-(triphenylmethyl)-2(E),4(Z)-heptadiene-1,6(S)-diol

Guidance literature:: With sodium iodide; In butanone; at 70 ℃;
DOI:10.1139/v87-244

Reference yield:

: 22900-10-3,35536-75-5,36792-85-5,113890-34-9,113890-37-2,133813-23-7
2-deoxy-D-ribose

: 111670-27-0
6-O-(tert-butyldiphenylsilyl)-7-iodo-1-O-(triphenylmethyl)-2(E),4(Z)-heptadiene-1,6(S)-diol

Guidance literature:: Multi-step reaction with 12 steps

2: (i-Pr)2NEt / DMAP / CH₂Cl₂

3: pyridine; CH₂Cl₂

4: DBU / pyridine

5: 92 percent / LDA / tetrahydrofuran / 0 °C

6: 89 percent / triphenylphosphine, DEAD / tetrahydrofuran / Ambient temperature

7: 79 percent / DIBAH / toluene / -10 deg C to room temp.

8: DMAP / pyridine / 50 °C

9: tetrabutylammonium fluoride / tetrahydrofuran / Ambient temperature

10: 63 percent / triethylamine / CH₂Cl₂ / Ambient temperature

11: 87 percent / (i-Pr)2NEt / CH₂Cl₂ / Ambient temperature

12: 83 percent / NaI / butan-2-one / 70 °C

With tetrabutyl ammonium fluoride; diisobutylaluminium hydride; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; N-ethyl-N,N-diisopropylamine; triphenylphosphine; sodium iodide; lithium diisopropyl amide; diethylazodicarboxylate; dmap; In tetrahydrofuran; pyridine; dichloromethane; toluene; butanone;
DOI:10.1139/v87-244

Reference yield:

: 79308-52-4
ethyl 2-[(4S,5R)-4-hydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl]acetate

: 111670-27-0
6-O-(tert-butyldiphenylsilyl)-7-iodo-1-O-(triphenylmethyl)-2(E),4(Z)-heptadiene-1,6(S)-diol

Guidance literature:: Multi-step reaction with 11 steps

1: (i-Pr)2NEt / DMAP / CH₂Cl₂

2: pyridine; CH₂Cl₂

3: DBU / pyridine

4: 92 percent / LDA / tetrahydrofuran / 0 °C

5: 89 percent / triphenylphosphine, DEAD / tetrahydrofuran / Ambient temperature

6: 79 percent / DIBAH / toluene / -10 deg C to room temp.

7: DMAP / pyridine / 50 °C

8: tetrabutylammonium fluoride / tetrahydrofuran / Ambient temperature

9: 63 percent / triethylamine / CH₂Cl₂ / Ambient temperature

10: 87 percent / (i-Pr)2NEt / CH₂Cl₂ / Ambient temperature

11: 83 percent / NaI / butan-2-one / 70 °C

With tetrabutyl ammonium fluoride; diisobutylaluminium hydride; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; N-ethyl-N,N-diisopropylamine; triphenylphosphine; sodium iodide; lithium diisopropyl amide; diethylazodicarboxylate; dmap; In tetrahydrofuran; pyridine; dichloromethane; toluene; butanone;
DOI:10.1139/v87-244