(2R,4aR,6S,7R,8S,8aS)-6-[(2R,3R,4S,5R,6R)-4,5-Bis-benzyloxy-6-benzyloxymethyl-2-((S)-1-pentyl-hex-5-enyloxy)-tetrahydro-pyran-3-yloxy]-7-(4-methoxy-benzyloxy)-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-8-ol

Base Information

Chemical Name:(2R,4aR,6S,7R,8S,8aS)-6-[(2R,3R,4S,5R,6R)-4,5-Bis-benzyloxy-6-benzyloxymethyl-2-((S)-1-pentyl-hex-5-enyloxy)-tetrahydro-pyran-3-yloxy]-7-(4-methoxy-benzyloxy)-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-8-ol
CAS No.:528603-38-5
Molecular Formula:C₅₉H₇₂O₁₂
Molecular Weight:973.213
Hs Code.:

(2R,4aR,6S,7R,8S,8aS)-6-[(2R,3R,4S,5R,6R)-4,5-Bis-benzyloxy-6-benzyloxymethyl-2-((S)-1-pentyl-hex-5-enyloxy)-tetrahydro-pyran-3-yloxy]-7-(4-methoxy-benzyloxy)-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-8-ol

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Chemical Property of (2R,4aR,6S,7R,8S,8aS)-6-[(2R,3R,4S,5R,6R)-4,5-Bis-benzyloxy-6-benzyloxymethyl-2-((S)-1-pentyl-hex-5-enyloxy)-tetrahydro-pyran-3-yloxy]-7-(4-methoxy-benzyloxy)-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-8-ol

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Technology Process of (2R,4aR,6S,7R,8S,8aS)-6-[(2R,3R,4S,5R,6R)-4,5-Bis-benzyloxy-6-benzyloxymethyl-2-((S)-1-pentyl-hex-5-enyloxy)-tetrahydro-pyran-3-yloxy]-7-(4-methoxy-benzyloxy)-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-8-ol

There total 8 articles about (2R,4aR,6S,7R,8S,8aS)-6-[(2R,3R,4S,5R,6R)-4,5-Bis-benzyloxy-6-benzyloxymethyl-2-((S)-1-pentyl-hex-5-enyloxy)-tetrahydro-pyran-3-yloxy]-7-(4-methoxy-benzyloxy)-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-8-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:

: 824-94-2
p-methoxybenzyl chloride

: 460745-19-1
(2R,4aR,6S,7R,8R,8aS)-6-[(2R,3R,4S,5R,6R)-4,5-Bis-benzyloxy-6-benzyloxymethyl-2-((S)-1-pentyl-hex-5-enyloxy)-tetrahydro-pyran-3-yloxy]-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxine-7,8-diol

: 528603-39-6
(2R,4aR,6S,7R,8R,8aR)-6-[(2R,3R,4S,5R,6R)-4,5-Bis-benzyloxy-6-benzyloxymethyl-2-((S)-1-pentyl-hex-5-enyloxy)-tetrahydro-pyran-3-yloxy]-8-(4-methoxy-benzyloxy)-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-ol

: 528603-38-5
(2R,4aR,6S,7R,8S,8aS)-6-[(2R,3R,4S,5R,6R)-4,5-Bis-benzyloxy-6-benzyloxymethyl-2-((S)-1-pentyl-hex-5-enyloxy)-tetrahydro-pyran-3-yloxy]-7-(4-methoxy-benzyloxy)-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-8-ol

Guidance literature:: (2R,4aR,6S,7R,8R,8aS)-6-[(2R,3R,4S,5R,6R)-4,5-Bis-benzyloxy-6-benzyloxymethyl-2-((S)-1-pentyl-hex-5-enyloxy)-tetrahydro-pyran-3-yloxy]-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxine-7,8-diol; With di(n-butyl)tin oxide; In toluene; for 4.5h; Heating;

p-methoxybenzyl chloride; With tetra-(n-butyl)ammonium iodide; cesium fluoride; In N,N-dimethyl-formamide; at 20 ℃; for 16h; Further stages.;
DOI:10.1002/chem.200390025

Reference yield:

: 53270-12-5
1,2-O-(1-ethoxyethylene) 3,4,6-tri-O-benzyl-1-thio-α-D-glucopyranose

: 528603-38-5
(2R,4aR,6S,7R,8S,8aS)-6-[(2R,3R,4S,5R,6R)-4,5-Bis-benzyloxy-6-benzyloxymethyl-2-((S)-1-pentyl-hex-5-enyloxy)-tetrahydro-pyran-3-yloxy]-7-(4-methoxy-benzyloxy)-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-8-ol

Guidance literature:: Multi-step reaction with 6 steps

1.1: aq. AcOH / 1 h / 20 °C

1.2: 92 percent / Cs₂CO₃ / CH₂Cl₂ / 14 h

2.1: 68 percent / BF₃*Et₂O / CH₂Cl₂; hexane / 2 h / -20 °C

3.1: 100 percent / NaOMe; MeOH

4.1: 82 percent / BF₃*Et₂O / diethyl ether; CH₂Cl₂ / 3.5 h / -20 - 20 °C

5.1: 88 percent / NaOMe; MeOH

6.1: Bu₂SnO / toluene / 4.5 h / Heating

6.2: CsF; nBu₄NI / dimethylformamide / 16 h / 20 °C

With methanol; boron trifluoride diethyl etherate; sodium methylate; di(n-butyl)tin oxide; acetic acid; In diethyl ether; hexane; dichloromethane; toluene;
DOI:10.1002/chem.200390025

Reference yield:

: 65827-55-6,68567-54-4,77790-45-5,77790-46-6,81969-44-0,99630-89-4,125135-30-0,137567-77-2,55628-56-3
1,2-di-O-acetyl-3,4,6-tri-O-benzyl-α-D-glucopyranoside

: 528603-38-5
(2R,4aR,6S,7R,8S,8aS)-6-[(2R,3R,4S,5R,6R)-4,5-Bis-benzyloxy-6-benzyloxymethyl-2-((S)-1-pentyl-hex-5-enyloxy)-tetrahydro-pyran-3-yloxy]-7-(4-methoxy-benzyloxy)-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-8-ol

Guidance literature:: Multi-step reaction with 7 steps

1.1: 90 percent / hydrazinium acetate / dimethylformamide / 0.25 h / 20 °C

2.1: 83 percent / Cs₂CO₃ / CH₂Cl₂ / 14 h

3.1: 68 percent / BF₃*Et₂O / CH₂Cl₂; hexane / 2 h / -20 °C

4.1: 100 percent / NaOMe; MeOH

5.1: 82 percent / BF₃*Et₂O / diethyl ether; CH₂Cl₂ / 3.5 h / -20 - 20 °C

6.1: 88 percent / NaOMe; MeOH

7.1: Bu₂SnO / toluene / 4.5 h / Heating

7.2: CsF; nBu₄NI / dimethylformamide / 16 h / 20 °C

With methanol; boron trifluoride diethyl etherate; sodium methylate; hydrazinium monoacetate; di(n-butyl)tin oxide; caesium carbonate; In diethyl ether; hexane; dichloromethane; N,N-dimethyl-formamide; toluene;
DOI:10.1002/chem.200390025