methyl 4,6-O-benzylidene-2-deoxy-2-C-methyl-3-O<(thiomethyl)-thiocarbonyl>-α-D-altro-pyranoside

Base Information

• Chemical Name: methyl 4,6-O-benzylidene-2-deoxy-2-C-methyl-3-O<(thiomethyl)-thiocarbonyl>-α-D-altro-pyranoside
• CAS No.: 68907-48-2
• Molecular Formula: C₁₇H₂₂O₅S₂
• Molecular Weight: 370.491

Synonyms:methyl 4,6-O-benzylidene-2-deoxy-2-C-methyl-3-O<(thiomethyl)-thiocarbonyl>-α-D-altro-pyranoside

Chemical Property of methyl 4,6-O-benzylidene-2-deoxy-2-C-methyl-3-O<(thiomethyl)-thiocarbonyl>-α-D-altro-pyranoside

Chemical Property:

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Technology Process of methyl 4,6-O-benzylidene-2-deoxy-2-C-methyl-3-O<(thiomethyl)-thiocarbonyl>-α-D-altro-pyranoside

There total 2 articles about methyl 4,6-O-benzylidene-2-deoxy-2-C-methyl-3-O<(thiomethyl)-thiocarbonyl>-α-D-altro-pyranoside 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:

carbon disulfide (75-15-0,12122-00-8) + methyl 4,6-O-benzylidene-2-deoxy-2-C-methyl-α-D-altro-pyranoside (68907-47-1) + methyl iodide (74-88-4) → methyl 4,6-O-benzylidene-2-deoxy-2-C-methyl-3-O<(thiomethyl)-thiocarbonyl>-α-D-altro-pyranoside (68907-48-2)

Guidance literature:

With 1H-imidazole; sodium hydride; In tetrahydrofuran;

DOI:10.1016/S0040-4039(02)00457-4

Reference yield:

carbon disulfide (75-15-0,12122-00-8) + Methyl 4,6-O-benzylidene-2-deoxy-2-methyl-α-D-glucopyranoside (130061-59-5) + methyl iodide (74-88-4) → Dithiocarbonic acid O-((2R,4aR,6S,7R,8R,8aS)-6-methoxy-7-methyl-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-8-yl) ester S-methyl ester (56981-18-1,68907-48-2)

Guidance literature:

With sodium hydride; Multistep reaction; 1) Et₂O, 3h, reflux;

DOI:10.1016/S0040-4039(00)88827-9

Reference yield: 90.0%

methyl 4,6-O-benzylidene-2-deoxy-2-C-methyl-3-O<(thiomethyl)-thiocarbonyl>-α-D-altro-pyranoside (68907-48-2) → methyl 4,6-O-benzylidene-2,3-dideoxy-2-C-methyl-α-D-arabino-hexopyranoside (68880-90-0)

Guidance literature:

With tri-n-butyl-tin hydride; In toluene; Heating;

DOI:10.1139/v82-050

upstream raw materials:

carbon disulfide

Methyl 4,6-O-benzylidene-2-deoxy-2-methyl-α-D-glucopyranoside

methyl iodide

methyl 4,6-O-benzylidene-2-deoxy-2-C-methyl-α-D-altro-pyranoside

Downstream raw materials:

(2R,4aR,6S,7R,8aS)-6-Methoxy-7-methyl-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxine

(2R,3S,5R,6S)-6-Methoxy-5-methyl-2-trityloxymethyl-tetrahydro-pyran-3-ol

(2S,3R,5S,6R)-2,5-Dimethoxy-3-methyl-6-trityloxymethyl-tetrahydro-pyran

methyl 4,6-O-benzylidene-2,3-dideoxy-2-C-methyl-α-D-arabino-hexopyranoside

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