Benzoic acid (2S,3R,4S,5R,6R)-4-allyloxy-2-[(2R,3R,4S,5R,6S)-3,5-diacetoxy-2-acetoxymethyl-6-(4-methoxy-phenoxy)-tetrahydro-pyran-4-yloxy]-5-hydroxy-6-hydroxymethyl-tetrahydro-pyran-3-yl ester

Base Information

• Chemical Name: Benzoic acid (2S,3R,4S,5R,6R)-4-allyloxy-2-[(2R,3R,4S,5R,6S)-3,5-diacetoxy-2-acetoxymethyl-6-(4-methoxy-phenoxy)-tetrahydro-pyran-4-yloxy]-5-hydroxy-6-hydroxymethyl-tetrahydro-pyran-3-yl ester
• CAS No.: 666258-35-1
• Molecular Formula: C₃₅H₄₂O₁₆
• Molecular Weight: 718.709

Synonyms:Benzoic acid (2S,3R,4S,5R,6R)-4-allyloxy-2-[(2R,3R,4S,5R,6S)-3,5-diacetoxy-2-acetoxymethyl-6-(4-methoxy-phenoxy)-tetrahydro-pyran-4-yloxy]-5-hydroxy-6-hydroxymethyl-tetrahydro-pyran-3-yl ester

Chemical Property of Benzoic acid (2S,3R,4S,5R,6R)-4-allyloxy-2-[(2R,3R,4S,5R,6S)-3,5-diacetoxy-2-acetoxymethyl-6-(4-methoxy-phenoxy)-tetrahydro-pyran-4-yloxy]-5-hydroxy-6-hydroxymethyl-tetrahydro-pyran-3-yl ester

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Technology Process of Benzoic acid (2S,3R,4S,5R,6R)-4-allyloxy-2-[(2R,3R,4S,5R,6S)-3,5-diacetoxy-2-acetoxymethyl-6-(4-methoxy-phenoxy)-tetrahydro-pyran-4-yloxy]-5-hydroxy-6-hydroxymethyl-tetrahydro-pyran-3-yl ester

There total 3 articles about Benzoic acid (2S,3R,4S,5R,6R)-4-allyloxy-2-[(2R,3R,4S,5R,6S)-3,5-diacetoxy-2-acetoxymethyl-6-(4-methoxy-phenoxy)-tetrahydro-pyran-4-yloxy]-5-hydroxy-6-hydroxymethyl-tetrahydro-pyran-3-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: 93.0%

4-methoxyphenyl 3-O-allyl-2-O-benzoyl-4,6-O-benzylidene-β-D-glucopyranosyl-(1->3)-2,4,6-tri-O-acetyl-β-D-glucopyranoside (666258-34-0) → Benzoic acid (2S,3R,4S,5R,6R)-4-allyloxy-2-[(2R,3R,4S,5R,6S)-3,5-diacetoxy-2-acetoxymethyl-6-(4-methoxy-phenoxy)-tetrahydro-pyran-4-yloxy]-5-hydroxy-6-hydroxymethyl-tetrahydro-pyran-3-yl ester (666258-35-1)

Guidance literature:

With acetic acid; for 2h; Heating;

DOI:10.1081/CAR-120026599

Reference yield:

4-methoxyphenyl 2,4,6-tri-O-acetyl-β-D-glucopyranoside → Benzoic acid (2S,3R,4S,5R,6R)-4-allyloxy-2-[(2R,3R,4S,5R,6S)-3,5-diacetoxy-2-acetoxymethyl-6-(4-methoxy-phenoxy)-tetrahydro-pyran-4-yloxy]-5-hydroxy-6-hydroxymethyl-tetrahydro-pyran-3-yl ester (666258-35-1)

Guidance literature:

Multi-step reaction with 2 steps

1: 74 percent / TMSOTf / CH₂Cl₂ / 3 h / -20 - 20 °C

2: 93 percent / aq. AcOH / 2 h / Heating

With trimethylsilyl trifluoromethanesulfonate; acetic acid; In dichloromethane;

DOI:10.1081/CAR-120026599

Reference yield:

Benzoic acid (2R,4aR,6R,7R,8S,8aR)-8-allyloxy-2-phenyl-6-(2,2,2-trichloro-acetimidoyloxy)-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl ester → Benzoic acid (2S,3R,4S,5R,6R)-4-allyloxy-2-[(2R,3R,4S,5R,6S)-3,5-diacetoxy-2-acetoxymethyl-6-(4-methoxy-phenoxy)-tetrahydro-pyran-4-yloxy]-5-hydroxy-6-hydroxymethyl-tetrahydro-pyran-3-yl ester (666258-35-1)

Guidance literature:

Multi-step reaction with 2 steps

1: 74 percent / TMSOTf / CH₂Cl₂ / 3 h / -20 - 20 °C

2: 93 percent / aq. AcOH / 2 h / Heating

With trimethylsilyl trifluoromethanesulfonate; acetic acid; In dichloromethane;

DOI:10.1081/CAR-120026599

upstream raw materials:

4-methoxyphenyl 3-O-allyl-2-O-benzoyl-4,6-O-benzylidene-β-D-glucopyranosyl-(1->3)-2,4,6-tri-O-acetyl-β-D-glucopyranoside

Downstream raw materials:

4-methoxyphenyl 2,4,6-tri-O-benzoyl-β-D-glucopyranosyl-(1->3)-2,4,6-tri-O-acetyl-β-D-glucopyranoside

C₄₉H₅₀O₁₈

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