(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

Base Information

• Chemical Name: (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
• CAS No.: 460745-19-1
• Molecular Formula: C₅₁H₆₄O₁₁
• Molecular Weight: 853.063

Synonyms:(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

Chemical Property of (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

Chemical Property:

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Safty Information:

• Pictogram(s):  
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Technology Process of (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

There total 8 articles about (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 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: 88.0%

Acetic acid (2R,4aR,6S,7R,8S,8aR)-8-acetoxy-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]dioxin-7-yl ester (460745-18-0) → (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 (460745-19-1)

Guidance literature:

With sodium methylate; In methanol;

DOI:10.1002/1521-3773(20020617)41

Reference yield:

3,4,6-tri-O-benzyl-2-O-acetyl-α-D-glucosyl trichloroimidate (108869-64-3) → (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 (460745-19-1)

Guidance literature:

Multi-step reaction with 4 steps

1: 68 percent / BF₃*Et₂O / CH₂Cl₂; hexane / 2 h / -20 °C

2: 100 percent / NaOMe; MeOH

3: 82 percent / BF₃*Et₂O / diethyl ether; CH₂Cl₂ / 3.5 h / -20 - 20 °C

4: 88 percent / NaOMe; MeOH

With methanol; boron trifluoride diethyl etherate; sodium methylate; In diethyl ether; hexane; dichloromethane;

DOI:10.1002/chem.200390025

Reference yield:

[(6S)-1-undecen-6-yl] 3,4,6-tri-O-benzyl-β-D-glucopyranoside (460745-17-9) → (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 (460745-19-1)

Guidance literature:

Multi-step reaction with 2 steps

1: 82 percent / BF₃*Et₂O / diethyl ether; CH₂Cl₂ / 3.5 h / -20 - 20 °C

2: 88 percent / NaOMe; MeOH

With methanol; boron trifluoride diethyl etherate; sodium methylate; In diethyl ether; dichloromethane;

DOI:10.1002/chem.200390025

upstream raw materials:

Acetic acid (2R,4aR,6S,7R,8S,8aR)-8-acetoxy-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]dioxin-7-yl ester

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

1,2-di-O-acetyl-3,4,6-tri-O-benzyl-α-D-glucopyranoside

2-O-acetyl-3,4,6-tri-O-benzyl-D-glucopyranose

Downstream raw materials:

(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

(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

acetic acid 8-acetoxy-6-{6-[4,5-bis-benzyloxy-6-benzyloxymethyl-2-(1-pentyl-hex-5-enyloxy)-tetrahydro-pyran-3-yloxy]-7-hydroxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-8-yloxy}-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl ester

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