(3R,4S,5R,6R)-6-benzyloxy-4,5-isopropylidenedioxy-2-phenyl-5-vinyloct-1-en-3-ol

Base Information

Chemical Name:(3R,4S,5R,6R)-6-benzyloxy-4,5-isopropylidenedioxy-2-phenyl-5-vinyloct-1-en-3-ol
CAS No.:795274-57-6
Molecular Formula:C₂₆H₃₂O₄
Molecular Weight:408.538
Hs Code.:

Synonyms:

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Chemical Property of (3R,4S,5R,6R)-6-benzyloxy-4,5-isopropylidenedioxy-2-phenyl-5-vinyloct-1-en-3-ol

Chemical Property:

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Technology Process of (3R,4S,5R,6R)-6-benzyloxy-4,5-isopropylidenedioxy-2-phenyl-5-vinyloct-1-en-3-ol

There total 11 articles about (3R,4S,5R,6R)-6-benzyloxy-4,5-isopropylidenedioxy-2-phenyl-5-vinyloct-1-en-3-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:

: 64638-65-9
5,6-dideoxy-1,2-O-isopropylidene-α-D-erythro-hexofuranos-3-ulose

: 795274-57-6
(3R,4S,5R,6R)-6-benzyloxy-4,5-isopropylidenedioxy-2-phenyl-5-vinyloct-1-en-3-ol

Guidance literature:: Multi-step reaction with 10 steps

1.1: tetrahydrofuran / 1 h / -18 °C

2.1: aq. AcOH / 11 h / 80 °C

3.1: 5.60 g / N-iodosuccinimide; n-Bu₄NI / CH₂Cl₂ / 20 h / 20 °C

4.1: 79 percent / CSA / acetone / 6 h / 40 °C / 225.02 Torr

5.1: 91 percent / LiAlH₄ / tetrahydrofuran / 2 h / 0 °C

6.1: DMAP; pyridine / 4 h / Heating

7.1: NaH / dimethylformamide / 8 h / 20 °C

8.1: 6.59 g / CSA / methanol / 48 h / 20 °C

9.1: 96 percent / Dess-Martin periodinane / CH₂Cl₂ / 3 h / 20 °C

10.1: tert-butyllithium / diethyl ether; pentane / 0.5 h / -78 °C

10.2: 94 percent / diethyl ether; pentane / 0.5 h / -78 °C

With pyridine; dmap; N-iodo-succinimide; lithium aluminium tetrahydride; camphor-10-sulfonic acid; tert.-butyl lithium; tetra-(n-butyl)ammonium iodide; sodium hydride; Dess-Martin periodane; acetic acid; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; N,N-dimethyl-formamide; acetone; pentane; 9.1: Dess-Martin oxidation;
DOI:10.1246/bcsj.77.1703

Reference yield:

: 16749-42-1
5,6-dideoxy-1,2-O-isopropylidene-α-D-xylo-hexofuranose

: 795274-57-6
(3R,4S,5R,6R)-6-benzyloxy-4,5-isopropylidenedioxy-2-phenyl-5-vinyloct-1-en-3-ol

Guidance literature:: Multi-step reaction with 11 steps

1.1: pyridinium chlorochromate; molecular sieves 4 Angstroem / CH₂Cl₂ / 10 h / 20 °C

2.1: tetrahydrofuran / 1 h / -18 °C

3.1: aq. AcOH / 11 h / 80 °C

4.1: 5.60 g / N-iodosuccinimide; n-Bu₄NI / CH₂Cl₂ / 20 h / 20 °C

5.1: 79 percent / CSA / acetone / 6 h / 40 °C / 225.02 Torr

6.1: 91 percent / LiAlH₄ / tetrahydrofuran / 2 h / 0 °C

7.1: DMAP; pyridine / 4 h / Heating

8.1: NaH / dimethylformamide / 8 h / 20 °C

9.1: 6.59 g / CSA / methanol / 48 h / 20 °C

10.1: 96 percent / Dess-Martin periodinane / CH₂Cl₂ / 3 h / 20 °C

11.1: tert-butyllithium / diethyl ether; pentane / 0.5 h / -78 °C

11.2: 94 percent / diethyl ether; pentane / 0.5 h / -78 °C

With pyridine; dmap; N-iodo-succinimide; lithium aluminium tetrahydride; 4 A molecular sieve; camphor-10-sulfonic acid; tert.-butyl lithium; tetra-(n-butyl)ammonium iodide; sodium hydride; Dess-Martin periodane; acetic acid; pyridinium chlorochromate; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; N,N-dimethyl-formamide; acetone; pentane; 10.1: Dess-Martin oxidation;
DOI:10.1246/bcsj.77.1703

Reference yield:

: 100-39-0
benzyl bromide

: 795274-57-6
(3R,4S,5R,6R)-6-benzyloxy-4,5-isopropylidenedioxy-2-phenyl-5-vinyloct-1-en-3-ol

Guidance literature:: Multi-step reaction with 4 steps

1.1: NaH / dimethylformamide / 8 h / 20 °C

2.1: 6.59 g / CSA / methanol / 48 h / 20 °C

3.1: 96 percent / Dess-Martin periodinane / CH₂Cl₂ / 3 h / 20 °C

4.1: tert-butyllithium / diethyl ether; pentane / 0.5 h / -78 °C

4.2: 94 percent / diethyl ether; pentane / 0.5 h / -78 °C

With camphor-10-sulfonic acid; tert.-butyl lithium; sodium hydride; Dess-Martin periodane; In methanol; diethyl ether; dichloromethane; N,N-dimethyl-formamide; pentane; 3.1: Dess-Martin oxidation;
DOI:10.1246/bcsj.77.1703