Acetic acid (2R,3R,4R,5S,6S)-4-allyloxy-5-benzyloxy-2-hydroxy-6-methyl-tetrahydro-pyran-3-yl ester

Base Information

• Chemical Name: Acetic acid (2R,3R,4R,5S,6S)-4-allyloxy-5-benzyloxy-2-hydroxy-6-methyl-tetrahydro-pyran-3-yl ester
• CAS No.: 152338-96-0
• Molecular Formula: C₁₈H₂₄O₆
• Molecular Weight: 336.385

Synonyms:Acetic acid (2R,3R,4R,5S,6S)-4-allyloxy-5-benzyloxy-2-hydroxy-6-methyl-tetrahydro-pyran-3-yl ester

Chemical Property of Acetic acid (2R,3R,4R,5S,6S)-4-allyloxy-5-benzyloxy-2-hydroxy-6-methyl-tetrahydro-pyran-3-yl ester

Chemical Property:

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Technology Process of Acetic acid (2R,3R,4R,5S,6S)-4-allyloxy-5-benzyloxy-2-hydroxy-6-methyl-tetrahydro-pyran-3-yl ester

There total 1 articles about Acetic acid (2R,3R,4R,5S,6S)-4-allyloxy-5-benzyloxy-2-hydroxy-6-methyl-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: 70.0%

1,2-di-O-acetyl-3-O-allyl-4-O-benzyl-α-L-rhamnopyranose (136933-81-8) → Acetic acid (2R,3R,4R,5S,6S)-4-allyloxy-5-benzyloxy-2-hydroxy-6-methyl-tetrahydro-pyran-3-yl ester (152338-96-0)

Guidance literature:

With tributyltin ethoxide; In dichloromethane; for 3h; Heating;

DOI:10.1016/0008-6215(93)84264-7

Reference yield: 73.0%

trichloroacetonitrile (545-06-2) + Acetic acid (2R,3R,4R,5S,6S)-4-allyloxy-5-benzyloxy-2-hydroxy-6-methyl-tetrahydro-pyran-3-yl ester (152338-96-0) → Acetic acid (2S,3R,4R,5S,6S)-4-allyloxy-5-benzyloxy-6-methyl-2-(2,2,2-trichloro-acetimidoyloxy)-tetrahydro-pyran-3-yl ester (152338-97-1)

Guidance literature:

With 1,8-diazabicyclo[5.4.0]undec-7-ene; In dichloromethane; for 0.166667h; Ambient temperature;

DOI:10.1016/0008-6215(93)84264-7

Reference yield:

Acetic acid (2R,3R,4R,5S,6S)-4-allyloxy-5-benzyloxy-2-hydroxy-6-methyl-tetrahydro-pyran-3-yl ester (152338-96-0) → methyl-3-O-(3-O-allyl-4-O-benzyl-α-L-rhamnopyranosyl)-2,4,6-tri-O-benzyl-β-D-glucopyranoside (152338-99-3)

Guidance literature:

Multi-step reaction with 3 steps

1: 73 percent / 1,8-diazobicyclo<5.4.0>undec-7-ene / CH₂Cl₂ / 0.17 h / Ambient temperature

2: 70 percent / BF₃*Et₂O, 4 A molecular sieves / CH₂Cl₂ / 0.5 h / -20 °C

3: 90 percent / NaOMe / methanol / 3 h

With 4 A molecular sieve; boron trifluoride diethyl etherate; sodium methylate; 1,8-diazabicyclo[5.4.0]undec-7-ene; In methanol; dichloromethane;

DOI:10.1016/0008-6215(93)84264-7

upstream raw materials:

1,2-di-O-acetyl-3-O-allyl-4-O-benzyl-α-L-rhamnopyranose

Downstream raw materials:

Acetic acid (2S,3R,4R,5S,6S)-4-allyloxy-5-benzyloxy-6-methyl-2-(2,2,2-trichloro-acetimidoyloxy)-tetrahydro-pyran-3-yl ester

methyl-3-O-(3-O-allyl-4-O-benzyl-α-L-rhamnopyranosyl)-2,4,6-tri-O-benzyl-β-D-glucopyranoside

methyl 2,4,6-tri-O-benzyl-3-O-(2,4-di-O-benzyl-α-L-rhamnopyranosyl)-β-D-glucopyranoside

Acetic acid (2S,3R,4R,5S,6S)-4-allyloxy-5-benzyloxy-2-((2R,3R,4S,5R,6R)-3,5-bis-benzyloxy-2-benzyloxymethyl-6-methoxy-tetrahydro-pyran-4-yloxy)-6-methyl-tetrahydro-pyran-3-yl ester

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