(2R,4R,6S)-4-Benzyloxy-2-((R)-2,5-bis-benzyloxy-pentyl)-6-iodomethyl-tetrahydro-pyran

Base Information

Chemical Name:(2R,4R,6S)-4-Benzyloxy-2-((R)-2,5-bis-benzyloxy-pentyl)-6-iodomethyl-tetrahydro-pyran
CAS No.:126461-73-2
Molecular Formula:C₃₂H₃₉IO₄
Molecular Weight:614.564
Hs Code.:

Synonyms:(2R,4R,6S)-4-Benzyloxy-2-((R)-2,5-bis-benzyloxy-pentyl)-6-iodomethyl-tetrahydro-pyran

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Chemical Property of (2R,4R,6S)-4-Benzyloxy-2-((R)-2,5-bis-benzyloxy-pentyl)-6-iodomethyl-tetrahydro-pyran

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Technology Process of (2R,4R,6S)-4-Benzyloxy-2-((R)-2,5-bis-benzyloxy-pentyl)-6-iodomethyl-tetrahydro-pyran

There total 10 articles about (2R,4R,6S)-4-Benzyloxy-2-((R)-2,5-bis-benzyloxy-pentyl)-6-iodomethyl-tetrahydro-pyran 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: 68.0%

: 126461-72-1
[(2S,4R,6R)-4-Benzyloxy-6-((R)-2,5-bis-benzyloxy-pentyl)-tetrahydro-pyran-2-yl]-methanol

: 126461-73-2
(2R,4R,6S)-4-Benzyloxy-2-((R)-2,5-bis-benzyloxy-pentyl)-6-iodomethyl-tetrahydro-pyran

Guidance literature:: With 1H-imidazole; iodine; triphenylphosphine; In toluene; for 3h; Ambient temperature;
DOI:10.1016/S0040-4039(01)80733-4

Reference yield:

: 100-39-0
benzyl bromide

: 126461-73-2
(2R,4R,6S)-4-Benzyloxy-2-((R)-2,5-bis-benzyloxy-pentyl)-6-iodomethyl-tetrahydro-pyran

Guidance literature:: Multi-step reaction with 8 steps

1: 93 percent / Bu₂SnO/NBu₄Br / toluene / 18 h / 80 °C

4: deacetylation

5: Ph₃P/DEAD/PhCOOH / tetrahydrofuran / Ambient temperature

6: NaH / dimethylformamide / 1 h / 0 °C

7: NBu₄F / tetrahydrofuran / 2 h / Ambient temperature

8: 68 percent / Ph₃P/imidazole/I₂ / toluene / 3 h / Ambient temperature

With 1H-imidazole; tetrabutyl ammonium fluoride; tetrabutylammomium bromide; iodine; sodium hydride; di(n-butyl)tin oxide; triphenylphosphine; benzoic acid; diethylazodicarboxylate; In tetrahydrofuran; N,N-dimethyl-formamide; toluene;
DOI:10.1016/S0040-4039(01)80733-4

Reference yield:

: 58871-09-3
6-O-tert-butyldimethylsilyl-D-glucal

: 126461-73-2
(2R,4R,6S)-4-Benzyloxy-2-((R)-2,5-bis-benzyloxy-pentyl)-6-iodomethyl-tetrahydro-pyran

Guidance literature:: Multi-step reaction with 8 steps

1: 93 percent / Bu₂SnO/NBu₄Br / toluene / 18 h / 80 °C

4: deacetylation

5: Ph₃P/DEAD/PhCOOH / tetrahydrofuran / Ambient temperature

6: NaH / dimethylformamide / 1 h / 0 °C

7: NBu₄F / tetrahydrofuran / 2 h / Ambient temperature

8: 68 percent / Ph₃P/imidazole/I₂ / toluene / 3 h / Ambient temperature

With 1H-imidazole; tetrabutyl ammonium fluoride; tetrabutylammomium bromide; iodine; sodium hydride; di(n-butyl)tin oxide; triphenylphosphine; benzoic acid; diethylazodicarboxylate; In tetrahydrofuran; N,N-dimethyl-formamide; toluene;
DOI:10.1016/S0040-4039(01)80733-4