(2R,3S,4S,5R,6S)-3,5-Bis-benzyloxy-2-benzyloxymethyl-6-fluoro-4-(4-methoxy-benzyloxy)-tetrahydro-pyran

Base Information

Chemical Name:(2R,3S,4S,5R,6S)-3,5-Bis-benzyloxy-2-benzyloxymethyl-6-fluoro-4-(4-methoxy-benzyloxy)-tetrahydro-pyran
CAS No.:165816-38-6
Molecular Formula:C₃₅H₃₇FO₆
Molecular Weight:572.674
Hs Code.:

Synonyms:(2R,3S,4S,5R,6S)-3,5-Bis-benzyloxy-2-benzyloxymethyl-6-fluoro-4-(4-methoxy-benzyloxy)-tetrahydro-pyran

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Chemical Property of (2R,3S,4S,5R,6S)-3,5-Bis-benzyloxy-2-benzyloxymethyl-6-fluoro-4-(4-methoxy-benzyloxy)-tetrahydro-pyran

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Technology Process of (2R,3S,4S,5R,6S)-3,5-Bis-benzyloxy-2-benzyloxymethyl-6-fluoro-4-(4-methoxy-benzyloxy)-tetrahydro-pyran

There total 11 articles about (2R,3S,4S,5R,6S)-3,5-Bis-benzyloxy-2-benzyloxymethyl-6-fluoro-4-(4-methoxy-benzyloxy)-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:

: 100-39-0
benzyl bromide

: 183730-72-5
(2S,3R,4R,5S,6R)-5-Benzyloxy-6-benzyloxymethyl-2-fluoro-4-(4-methoxy-benzyloxy)-tetrahydro-pyran-3-ol

: 165816-38-6
(2R,3S,4S,5R,6S)-3,5-Bis-benzyloxy-2-benzyloxymethyl-6-fluoro-4-(4-methoxy-benzyloxy)-tetrahydro-pyran

Guidance literature:: With sodium hydride; In N,N-dimethyl-formamide; at 0 - 20 ℃; for 1h; Yield given;
DOI:10.1021/ja962048b

Reference yield:

: 165816-37-5
4,6-di-O-benzyl-3-O-(4-methoxybenzyl)-D-galactal

: 165816-38-6
(2R,3S,4S,5R,6S)-3,5-Bis-benzyloxy-2-benzyloxymethyl-6-fluoro-4-(4-methoxy-benzyloxy)-tetrahydro-pyran

Guidance literature:: Multi-step reaction with 3 steps

1: dimethyldioxirane / CH₂Cl₂ / 0 °C

2: 2.06 g / pyridine*HF; molecular sieves 4 Angstroem / tetrahydrofuran / 0 - 20 °C

3: NaH; molecular sieves 4 Angstroem / dimethylformamide / 20 °C

With 4 A molecular sieve; 3,3-dimethyldioxirane; sodium hydride; pyridine hydrogenfluoride; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide; 1: Epoxidation / 2: Ring cleavage / 3: Etherification;
DOI:10.1002/(SICI)1521-3765(20000417)6:8<1366::AID-CHEM1366>3.0.CO;2-K

Reference yield:

: 183730-71-4
3-O-(4-methoxybenzyl)-D-galactal

: 165816-38-6
(2R,3S,4S,5R,6S)-3,5-Bis-benzyloxy-2-benzyloxymethyl-6-fluoro-4-(4-methoxy-benzyloxy)-tetrahydro-pyran

Guidance literature:: Multi-step reaction with 4 steps

1: 96 percent / NaH / dimethylformamide / 1.5 h / 0 - 20 °C

2: 3,3'-dimethyldioxirane / CH₂Cl₂ / 1 h / 0 °C

3: TBAF / tetrahydrofuran / 20 h / Ambient temperature

4: NaH / dimethylformamide / 1 h / 0 - 20 °C

With tetrabutyl ammonium fluoride; 3,3-dimethyldioxirane; sodium hydride; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1021/ja962048b