(2R,3S,4aR,6R,8S,8aS)-8-Benzyloxy-6-(3-benzyloxy-propyl)-2-hydroxymethyl-2-methyl-octahydro-pyrano[3,2-b]pyran-3-ol

Base Information

Chemical Name:(2R,3S,4aR,6R,8S,8aS)-8-Benzyloxy-6-(3-benzyloxy-propyl)-2-hydroxymethyl-2-methyl-octahydro-pyrano[3,2-b]pyran-3-ol
CAS No.:189348-00-3
Molecular Formula:C₂₇H₃₆O₆
Molecular Weight:456.579
Hs Code.:

Synonyms:(2R,3S,4aR,6R,8S,8aS)-8-Benzyloxy-6-(3-benzyloxy-propyl)-2-hydroxymethyl-2-methyl-octahydro-pyrano[3,2-b]pyran-3-ol

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Chemical Property of (2R,3S,4aR,6R,8S,8aS)-8-Benzyloxy-6-(3-benzyloxy-propyl)-2-hydroxymethyl-2-methyl-octahydro-pyrano[3,2-b]pyran-3-ol

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Technology Process of (2R,3S,4aR,6R,8S,8aS)-8-Benzyloxy-6-(3-benzyloxy-propyl)-2-hydroxymethyl-2-methyl-octahydro-pyrano[3,2-b]pyran-3-ol

There total 14 articles about (2R,3S,4aR,6R,8S,8aS)-8-Benzyloxy-6-(3-benzyloxy-propyl)-2-hydroxymethyl-2-methyl-octahydro-pyrano[3,2-b]pyran-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: 98.0%

: 213747-16-1
(2R,3S,4aR,6R,8S,8aS)-8-Benzyloxy-6-(3-benzyloxy-propyl)-2-(tert-butyl-diphenyl-silanyloxymethyl)-2-methyl-octahydro-pyrano[3,2-b]pyran-3-ol

: 189348-00-3
(2R,3S,4aR,6R,8S,8aS)-8-Benzyloxy-6-(3-benzyloxy-propyl)-2-hydroxymethyl-2-methyl-octahydro-pyrano[3,2-b]pyran-3-ol

Guidance literature:: With tetrabutyl ammonium fluoride; In tetrahydrofuran;
DOI:10.1021/ja9701523

Reference yield:

: 189347-91-9
benzyl 3-(3-O-benzyl-2-deoxy-α-D-allopyranosyl)propyl ether

: 189348-00-3
(2R,3S,4aR,6R,8S,8aS)-8-Benzyloxy-6-(3-benzyloxy-propyl)-2-hydroxymethyl-2-methyl-octahydro-pyrano[3,2-b]pyran-3-ol

Guidance literature:: Multi-step reaction with 5 steps

1: 1.) 2,6-lutidine / 1.) CH₂Cl₂, -78 deg C, 30 min, 2.) -78 deg C, 30 min

2: 90 percent / n-BuLi / hexamethylphosphoric acid triamide; tetrahydrofuran; hexane / 1.) -100 deg C, 10 min, 2.) -80 deg C, 10 min

3: 90 percent / p-TsOH*H₂O / CHCl₃ / 1.) 0 deg C, 30 min, 2.) room temperature, 3 h

4: 92 percent / NaBH₄ / methanol; CH₂Cl₂ / 2 h / -78 °C

5: 98 percent / Bu₄NF / tetrahydrofuran / 2 h / Ambient temperature

With 2,6-dimethylpyridine; sodium tetrahydroborate; n-butyllithium; tetrabutyl ammonium fluoride; toluene-4-sulfonic acid; In tetrahydrofuran; methanol; N,N,N,N,N,N-hexamethylphosphoric triamide; hexane; dichloromethane; chloroform;
DOI:10.1021/jo980320p

Reference yield:

: 189347-96-4
Trifluoro-methanesulfonic acid (2R,3S,4S,6R)-4-benzyloxy-6-(3-benzyloxy-propyl)-3-triethylsilanyloxy-tetrahydro-pyran-2-ylmethyl ester

: 189348-00-3
(2R,3S,4aR,6R,8S,8aS)-8-Benzyloxy-6-(3-benzyloxy-propyl)-2-hydroxymethyl-2-methyl-octahydro-pyrano[3,2-b]pyran-3-ol

Guidance literature:: Multi-step reaction with 4 steps

1: 90 percent / n-BuLi / hexamethylphosphoric acid triamide; tetrahydrofuran; hexane / 1.) -100 deg C, 10 min, 2.) -80 deg C, 10 min

2: 90 percent / p-TsOH*H₂O / CHCl₃ / 1.) 0 deg C, 30 min, 2.) room temperature, 3 h

3: 92 percent / NaBH₄ / methanol; CH₂Cl₂ / 2 h / -78 °C

4: 98 percent / Bu₄NF / tetrahydrofuran / 2 h / Ambient temperature

With sodium tetrahydroborate; n-butyllithium; tetrabutyl ammonium fluoride; toluene-4-sulfonic acid; In tetrahydrofuran; methanol; N,N,N,N,N,N-hexamethylphosphoric triamide; hexane; dichloromethane; chloroform;
DOI:10.1021/jo980320p