Acetic acid (2R,3S,4R,4aS,5S,6S,8aS)-2-acetoxymethyl-4,5,6-tris-benzyloxy-6-methyl-hexahydro-pyrano[2,3-b]pyran-3-yl ester

Base Information

• Chemical Name: Acetic acid (2R,3S,4R,4aS,5S,6S,8aS)-2-acetoxymethyl-4,5,6-tris-benzyloxy-6-methyl-hexahydro-pyrano[2,3-b]pyran-3-yl ester
• CAS No.: 117300-06-8
• Molecular Formula: C₃₅H₄₀O₉
• Molecular Weight: 604.697

Synonyms:Acetic acid (2R,3S,4R,4aS,5S,6S,8aS)-2-acetoxymethyl-4,5,6-tris-benzyloxy-6-methyl-hexahydro-pyrano[2,3-b]pyran-3-yl ester

Chemical Property of Acetic acid (2R,3S,4R,4aS,5S,6S,8aS)-2-acetoxymethyl-4,5,6-tris-benzyloxy-6-methyl-hexahydro-pyrano[2,3-b]pyran-3-yl ester

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Technology Process of Acetic acid (2R,3S,4R,4aS,5S,6S,8aS)-2-acetoxymethyl-4,5,6-tris-benzyloxy-6-methyl-hexahydro-pyrano[2,3-b]pyran-3-yl ester

There total 1 articles about Acetic acid (2R,3S,4R,4aS,5S,6S,8aS)-2-acetoxymethyl-4,5,6-tris-benzyloxy-6-methyl-hexahydro-pyrano[2,3-b]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:

acetic anhydride (108-24-7) + 3-O-benzyl-2-deoxy-2-C-(L-threo-1',2'-dibenzyloxy-2'-methylpropane-1',3'-diyl)-α-D-glucopyranoside (110046-71-4) → Acetic acid (2R,3S,4R,4aS,5S,6S,8aS)-2-acetoxymethyl-4,5,6-tris-benzyloxy-6-methyl-hexahydro-pyrano[2,3-b]pyran-3-yl ester (117300-06-8)

Guidance literature:

With dmap; In ethyl acetate; Ambient temperature;

DOI:10.1016/0008-6215(88)85084-5

Reference yield: 70.0%

acetic anhydride (108-24-7) + Acetic acid (2R,3S,4R,4aS,5S,6S,8aS)-2-acetoxymethyl-4,5,6-tris-benzyloxy-6-methyl-hexahydro-pyrano[2,3-b]pyran-3-yl ester (117300-06-8) → 2-C-(L-threo-3'-acetoxy-1'-benzyloxy-2'-methylpropane-1',2'-diyl)-4,6-di-O-acetyl-3-O-benzyl-2-deoxy-α-D-glucopyranoside (117300-07-9)

Guidance literature:

boron trifluoride diethyl etherate; at 0 ℃; for 0.166667h;

DOI:10.1016/0008-6215(88)85084-5

Reference yield: 60.0%

acetic anhydride (108-24-7) + Acetic acid (2R,3S,4R,4aS,5S,6S,8aS)-2-acetoxymethyl-4,5,6-tris-benzyloxy-6-methyl-hexahydro-pyrano[2,3-b]pyran-3-yl ester (117300-06-8) → Acetic acid (2S,3S,4R,5S,6R,7aR)-2,6-bis-acetoxymethyl-3,4-bis-benzyloxy-2-methyl-hexahydro-furo[2,3-b]pyran-5-yl ester

Guidance literature:

With boron trifluoride diethyl etherate; at 0 ℃; for 0.166667h;

DOI:10.1039/c39860001570

upstream raw materials:

acetic anhydride

3-O-benzyl-2-deoxy-2-C-(L-threo-1',2'-dibenzyloxy-2'-methylpropane-1',3'-diyl)-α-D-glucopyranoside

Downstream raw materials:

2-C-(L-threo-3'-acetoxy-1'-benzyloxy-2'-methylpropane-1',2'-diyl)-4,6-di-O-acetyl-3-O-benzyl-2-deoxy-α-D-glucopyranoside

1,5-di-O-acetyl-3-O-benzyl-2-deoxy-4-C-methyl-2-C-(L-lyxo-2',3',4'-triacetoxy-1'-benzyloxybutyl)-β-L-arabinofuranose

1,5-di-O-acetyl-3-O-benzyl-2-deoxy-4-C-methyl-2-C-(L-lyxo-2',3',4'-triacetoxy-1'-benzyloxybutyl)-α-L-arabinofuranose

1,5-di-O-acetyl-3-O-benzyl-2-deoxy-4-C-methyl-2-C-(L-lyxo-2',3',4'-triacetoxy-1'-benzyloxybutyl)-α,β-L-arabinofuranose

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