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

Base Information

• Chemical Name: 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
• CAS No.: 460745-18-0
• Molecular Formula: C₅₅H₆₈O₁₃
• Molecular Weight: 937.137

Synonyms: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

Chemical Property of 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

Chemical Property:

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Technology Process of 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

There total 7 articles about 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 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: 82.0%

2,3-di-O-acetyl-4,6-O-benzylidene-D-glucopyranosyl trichloroacetimidate (206866-61-7) + [(6S)-1-undecen-6-yl] 3,4,6-tri-O-benzyl-β-D-glucopyranoside (460745-17-9) → 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)

Guidance literature:

With boron trifluoride diethyl etherate; In hexane; dichloromethane; at -20 ℃;

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) → 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)

Guidance literature:

Multi-step reaction with 3 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

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] 2-O-acetyl-3,4,6-tri-O-benzyl-β-D-glucopyranoside (460745-16-8) → 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)

Guidance literature:

Multi-step reaction with 2 steps

1: 100 percent / NaOMe; MeOH

2: 82 percent / BF₃*Et₂O / diethyl ether; CH₂Cl₂ / 3.5 h / -20 - 20 °C

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

DOI:10.1002/chem.200390025

upstream raw materials:

2,3-di-O-acetyl-4,6-O-benzylidene-D-glucopyranosyl trichloroacetimidate

[(6S)-1-undecen-6-yl] 3,4,6-tri-O-benzyl-β-D-glucopyranoside

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

Downstream raw materials:

(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

(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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