(3R,5R)-5-benzyloxy-1-iodo-3-(tert-butyldimethylsilanyloxy)-6-(tert-butyldiphenylsilanyloxy)hexane

Base Information

Chemical Name:(3R,5R)-5-benzyloxy-1-iodo-3-(tert-butyldimethylsilanyloxy)-6-(tert-butyldiphenylsilanyloxy)hexane
CAS No.:913193-75-6
Molecular Formula:C₃₅H₅₁IO₃Si₂
Molecular Weight:702.864
Hs Code.:

Synonyms:(3R,5R)-5-benzyloxy-1-iodo-3-(tert-butyldimethylsilanyloxy)-6-(tert-butyldiphenylsilanyloxy)hexane

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Chemical Property of (3R,5R)-5-benzyloxy-1-iodo-3-(tert-butyldimethylsilanyloxy)-6-(tert-butyldiphenylsilanyloxy)hexane

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Technology Process of (3R,5R)-5-benzyloxy-1-iodo-3-(tert-butyldimethylsilanyloxy)-6-(tert-butyldiphenylsilanyloxy)hexane

There total 9 articles about (3R,5R)-5-benzyloxy-1-iodo-3-(tert-butyldimethylsilanyloxy)-6-(tert-butyldiphenylsilanyloxy)hexane 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: 92.0%

: 913193-74-5
(3S,5R)-5-benzyloxy-3-(tert-butyldimethylsilanyloxy)-6-(tert-butyldiphenylsilanyloxy)hexan-1-ol

: 913193-75-6
(3R,5R)-5-benzyloxy-1-iodo-3-(tert-butyldimethylsilanyloxy)-6-(tert-butyldiphenylsilanyloxy)hexane

Guidance literature:: With methyltriphenoxyphosphonium iodide; In N,N-dimethyl-formamide; at 0 ℃; for 1h;
DOI:10.1021/jo0610412

Reference yield:

: 913193-72-3
(3R)-3-benzyloxy-4-(tert-butyldiphenylsilanyloxy)butyraldehyde

: 913193-75-6
(3R,5R)-5-benzyloxy-1-iodo-3-(tert-butyldimethylsilanyloxy)-6-(tert-butyldiphenylsilanyloxy)hexane

Guidance literature:: Multi-step reaction with 5 steps

1.1: 80 percent / TiCl₄ / CH₂Cl₂ / 0.33 h / -78 °C

2.1: 97 percent / 2,6-lutidine / CH₂Cl₂ / 2 h / 0 °C

3.1: O₃; pyridine / methanol; CH₂Cl₂ / 0.75 h / -78 °C

3.2: 99 percent / Me₂S / methanol; CH₂Cl₂ / 12 h / -78 - 20 °C

4.1: 95 percent / NaBH₄ / methanol / 0.33 h / 0 °C

5.1: 92 percent / (PhO)3PCH₃⁽¹⁺⁾*I^(1-) / dimethylformamide / 1 h / 0 °C

With pyridine; 2,6-dimethylpyridine; sodium tetrahydroborate; methyltriphenoxyphosphonium iodide; titanium tetrachloride; ozone; In methanol; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1021/jo0610412

Reference yield:

: (6R)-6-benzyloxy-7-(tert-butyldiphenylsilanyloxy)hept-1-en-4-ol

: 913193-75-6
(3R,5R)-5-benzyloxy-1-iodo-3-(tert-butyldimethylsilanyloxy)-6-(tert-butyldiphenylsilanyloxy)hexane

Guidance literature:: Multi-step reaction with 4 steps

1.1: 97 percent / 2,6-lutidine / CH₂Cl₂ / 2 h / 0 °C

2.1: O₃; pyridine / methanol; CH₂Cl₂ / 0.75 h / -78 °C

2.2: 99 percent / Me₂S / methanol; CH₂Cl₂ / 12 h / -78 - 20 °C

3.1: 95 percent / NaBH₄ / methanol / 0.33 h / 0 °C

4.1: 92 percent / (PhO)3PCH₃⁽¹⁺⁾*I^(1-) / dimethylformamide / 1 h / 0 °C

With pyridine; 2,6-dimethylpyridine; sodium tetrahydroborate; methyltriphenoxyphosphonium iodide; ozone; In methanol; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1021/jo0610412