(2R,4aR,6S,8S,8aS)-6-Methoxy-2-phenyl-8-[1,2,4]trioxolan-3-ylmethyl-tetrahydro-pyrano[3,2-d][1,3]dioxin-7-one

Base Information

• Chemical Name: (2R,4aR,6S,8S,8aS)-6-Methoxy-2-phenyl-8-[1,2,4]trioxolan-3-ylmethyl-tetrahydro-pyrano[3,2-d][1,3]dioxin-7-one
• CAS No.: 838838-30-5
• Molecular Formula: C₁₇H₂₀O₈
• Molecular Weight: 352.341

Synonyms:(2R,4aR,6S,8S,8aS)-6-Methoxy-2-phenyl-8-[1,2,4]trioxolan-3-ylmethyl-tetrahydro-pyrano[3,2-d][1,3]dioxin-7-one

Chemical Property of (2R,4aR,6S,8S,8aS)-6-Methoxy-2-phenyl-8-[1,2,4]trioxolan-3-ylmethyl-tetrahydro-pyrano[3,2-d][1,3]dioxin-7-one

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Technology Process of (2R,4aR,6S,8S,8aS)-6-Methoxy-2-phenyl-8-[1,2,4]trioxolan-3-ylmethyl-tetrahydro-pyrano[3,2-d][1,3]dioxin-7-one

There total 1 articles about (2R,4aR,6S,8S,8aS)-6-Methoxy-2-phenyl-8-[1,2,4]trioxolan-3-ylmethyl-tetrahydro-pyrano[3,2-d][1,3]dioxin-7-one 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: 85.0%

methyl 4,6-O-benzylidene-3-deoxy-3-C-propenyl-α-D-arabino-hexopyranoside-2-ulose (135700-48-0) → (2R,4aR,6S,8S,8aS)-6-Methoxy-2-phenyl-8-[1,2,4]trioxolan-3-ylmethyl-tetrahydro-pyrano[3,2-d][1,3]dioxin-7-one (838838-30-5)

Guidance literature:

With ozone; In dichloromethane; at 20 ℃; for 1h;

DOI:10.1016/j.tetlet.2004.11.032

Reference yield: 83.0%

(2R,4aR,6S,8S,8aS)-6-Methoxy-2-phenyl-8-[1,2,4]trioxolan-3-ylmethyl-tetrahydro-pyrano[3,2-d][1,3]dioxin-7-one (838838-30-5) → (2R,4aR,6S,7R,8R,8aS)-6-Methoxy-2-phenyl-8-[1,2,4]trioxolan-3-ylmethyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-ol

Guidance literature:

With sodium cyanoborohydride; In tetrahydrofuran; dichloromethane; at 20 ℃; for 1h;

DOI:10.1016/j.tetlet.2004.11.032

Reference yield: 62.0%

(2R,4aR,6S,8S,8aS)-6-Methoxy-2-phenyl-8-[1,2,4]trioxolan-3-ylmethyl-tetrahydro-pyrano[3,2-d][1,3]dioxin-7-one (838838-30-5) → methyl α-D-4,6-O-((R)-benzylidene)-3-deoxy-3-(2-oxoethyl)-glucopyranosid-2-ulose (838838-31-6)

Guidance literature:

With polymer-bound PPh₃; In toluene; at 90 ℃; for 1h;

DOI:10.1016/j.tetlet.2004.11.032

upstream raw materials:

methyl 4,6-O-benzylidene-3-deoxy-3-C-propenyl-α-D-arabino-hexopyranoside-2-ulose

Downstream raw materials:

methyl α-D-4,6-O-((R)-benzylidene)-3-deoxy-3-(2-oxoethyl)-glucopyranosid-2-ulose

methyl α-D-2-amino-4,6-O-((R)-benzylidene)-2,3-dideoxy-2-N,3-C-(ethane-1,2-diyl)-2-N-hydroxy-mannopyranoside

methyl α-D-2-amino-4,6-O-((R)-benzylidene)-2,3-dideoxy-2-N,3-C-(ethane-1,2-diyl)-2-N-isopropyl-mannopyranoside

methyl α-D-2-amino-4,6-O-((R)-benzylidene)-2,3-dideoxy-2-N,3-C-(ethane-1,2-diyl)-2-N-(3-hydroxy-propyl)-mannopyranoside

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