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

Base Information

• Chemical Name: Acetic acid (2R,3S,4S,5R,6R)-3,5-bis-benzyloxy-2-benzyloxymethyl-6-hydroxy-tetrahydro-pyran-4-yl ester
• CAS No.: 127875-29-0
• Molecular Formula: C₂₉H₃₂O₇
• Molecular Weight: 492.569

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

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

Chemical Property:

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

There total 18 articles about Acetic acid (2R,3S,4S,5R,6R)-3,5-bis-benzyloxy-2-benzyloxymethyl-6-hydroxy-tetrahydro-pyran-4-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: 92.0%

Acetic acid (3R,4S,5R,6R)-2-acetoxy-3,5-bis-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-4-yl ester (61236-89-3,77364-22-8,78185-10-1,78185-11-2,84620-68-8,84620-69-9,89104-66-5,89104-67-6) → 3-O-acetyl-2,4,6-tri-O-benzyl-D-glycopyranose (127873-80-7,127873-97-6,127874-23-1,127875-22-3,127875-29-0,127875-36-9)

Guidance literature:

With hydrazinium monoacetate; In N,N-dimethyl-formamide; at 40 ℃; for 2h; Inert atmosphere;

DOI:10.1039/c9cc07915g

Reference yield: 81.0%

2-propenyl 6-O-acetyl-2,4,6-tri-O-benzyl-β-D-galactopyranoside (125790-92-3) → Acetic acid (2R,3S,4S,5R,6R)-3,5-bis-benzyloxy-2-benzyloxymethyl-6-hydroxy-tetrahydro-pyran-4-yl ester (127875-29-0)

Guidance literature:

2-propenyl 6-O-acetyl-2,4,6-tri-O-benzyl-β-D-galactopyranoside; With RhCl(PPh₃)3; In ethanol; water; toluene; for 20h; Heating;

With hydrogenchloride; for 1h; Heating;

DOI:10.1016/S0008-6215(01)00222-1

Reference yield: 60.0%

2-methoxyethyl 3-O-acetyl-2,4,6-tri-O-benzyl-β-D-glucopyranoside (87908-35-8) → 3-O-acetyl-2,4,6-tri-O-benzyl-D-glycopyranose (127873-80-7,127873-97-6,127874-23-1,127875-22-3,127875-29-0,127875-36-9)

Guidance literature:

With titanium tetrachloride; In dichloromethane; for 0.0833333h; Ambient temperature;

DOI:10.1246/bcsj.62.3549

upstream raw materials:

2-methoxyethyl 3-O-acetyl-2,4,6-tri-O-benzyl-β-D-glucopyranoside

2-methoxyethyl 2,4,6-tri-O-benzyl-β-D-glucopyranoside

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

(2R,3S,4S,5R,6S)-3,5-Bis-benzyloxy-2-benzyloxymethyl-6-methoxy-tetrahydro-pyran-4-ol

Downstream raw materials:

3-O-acetyl-2,4,6-tri-O-benzyl-β-D-galactopyranosyl trichloroacetimidate

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

2-propenyl 2,4-O-benzyl-3-O-(2,4,6-tri-O-benzyl-α-D-galactopyranosyl)-β-D-galactopyranoside

O-(3-O-acetyl-2,4,6-tri-O-benzyl-α-D-glucopyranosyl) N-phenyltrifluoroacetimidate

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