Acetic acid (2R,3S,5R,6S)-5-benzyloxy-3-hydroxy-6-methoxy-tetrahydro-pyran-2-ylmethyl ester

Base Information

• Chemical Name: Acetic acid (2R,3S,5R,6S)-5-benzyloxy-3-hydroxy-6-methoxy-tetrahydro-pyran-2-ylmethyl ester
• CAS No.: 178621-76-6
• Molecular Formula: C₁₆H₂₂O₆
• Molecular Weight: 310.347

Synonyms:Acetic acid (2R,3S,5R,6S)-5-benzyloxy-3-hydroxy-6-methoxy-tetrahydro-pyran-2-ylmethyl ester

Chemical Property of Acetic acid (2R,3S,5R,6S)-5-benzyloxy-3-hydroxy-6-methoxy-tetrahydro-pyran-2-ylmethyl ester

Chemical Property:

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Technology Process of Acetic acid (2R,3S,5R,6S)-5-benzyloxy-3-hydroxy-6-methoxy-tetrahydro-pyran-2-ylmethyl ester

There total 2 articles about Acetic acid (2R,3S,5R,6S)-5-benzyloxy-3-hydroxy-6-methoxy-tetrahydro-pyran-2-ylmethyl 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: 91.7%

acetyl chloride (75-36-5) + methyl 2-O-benzyl-3,6-dideoxy-α-D-ribo-hexopyranoside (50272-15-6) → Acetic acid (2R,3S,5R,6S)-5-benzyloxy-3-hydroxy-6-methoxy-tetrahydro-pyran-2-ylmethyl ester (178621-76-6)

Guidance literature:

With 2,4,6-trimethyl-pyridine; at -40 ℃; for 0.666667h;

DOI:10.1016/0008-6215(96)00005-5

Reference yield:

methyl 2-O-benzyl-4,6-O-benzylidene-3-deoxy-α-D-ribo-hexopyranoside (50272-14-5) → Acetic acid (2R,3S,5R,6S)-5-benzyloxy-3-hydroxy-6-methoxy-tetrahydro-pyran-2-ylmethyl ester (178621-76-6)

Guidance literature:

Multi-step reaction with 2 steps

1: 91 percent / 5percent HCl in MeOH / 0.33 h

2: 91.7 percent / sym-collidine / 0.67 h / -40 °C

With 2,4,6-trimethyl-pyridine; hydrogenchloride;

DOI:10.1016/0008-6215(96)00005-5

Reference yield: 93.3%

benzoyl chloride (98-88-4) + Acetic acid (2R,3S,5R,6S)-5-benzyloxy-3-hydroxy-6-methoxy-tetrahydro-pyran-2-ylmethyl ester (178621-76-6) → Benzoic acid (2R,3S,5R,6S)-2-acetoxymethyl-5-benzyloxy-6-methoxy-tetrahydro-pyran-3-yl ester (178621-77-7)

Guidance literature:

With pyridine; Ambient temperature;

DOI:10.1016/0008-6215(96)00005-5

upstream raw materials:

acetyl chloride

methyl 2-O-benzyl-3,6-dideoxy-α-D-ribo-hexopyranoside

methyl 2-O-benzyl-4,6-O-benzylidene-3-deoxy-α-D-ribo-hexopyranoside

Downstream raw materials:

Benzoic acid (2R,3S,5R,6S)-2-acetoxymethyl-5-benzyloxy-6-methoxy-tetrahydro-pyran-3-yl ester

Benzoic acid (2R,3S,5R,6S)-5-benzyloxy-2-hydroxymethyl-6-methoxy-tetrahydro-pyran-3-yl ester

Benzoic acid (2R,3S,5R,6S)-5-benzyloxy-6-methoxy-2-trimethylsilanyloxymethyl-tetrahydro-pyran-3-yl ester

(2R,3S,5R,6S)-5-Benzyloxy-2-((2S,3R,5S,6R)-3,5-bis-benzyloxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxymethyl)-6-methoxy-tetrahydro-pyran-3-ol

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