methyl 3,7-anhydro-4,5,6-tri-O-benzyl-2-deoxy-8-O-mesyl-D-gulo-D-glycero-octulonate

Base Information

Chemical Name:methyl 3,7-anhydro-4,5,6-tri-O-benzyl-2-deoxy-8-O-mesyl-D-gulo-D-glycero-octulonate
CAS No.:603129-44-8
Molecular Formula:C₃₁H₃₆O₉S
Molecular Weight:584.687
Hs Code.:

Synonyms:methyl 3,7-anhydro-4,5,6-tri-O-benzyl-2-deoxy-8-O-mesyl-D-gulo-D-glycero-octulonate

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Chemical Property of methyl 3,7-anhydro-4,5,6-tri-O-benzyl-2-deoxy-8-O-mesyl-D-gulo-D-glycero-octulonate

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Technology Process of methyl 3,7-anhydro-4,5,6-tri-O-benzyl-2-deoxy-8-O-mesyl-D-gulo-D-glycero-octulonate

There total 6 articles about methyl 3,7-anhydro-4,5,6-tri-O-benzyl-2-deoxy-8-O-mesyl-D-gulo-D-glycero-octulonate 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: 100.0%

: 124-63-0
methanesulfonyl chloride

: 578764-42-8
methyl 3,7-anhydro-4,5,6-tri-O-benzyl-2-deoxy-D-gulo-D-glycero-octulonate

: 603129-44-8
methyl 3,7-anhydro-4,5,6-tri-O-benzyl-2-deoxy-8-O-mesyl-D-gulo-D-glycero-octulonate

Guidance literature:: In pyridine; for 16h;
DOI:10.1002/ejoc.200300031

Reference yield:

: 34010-29-2
2-((2S,3S,4R,5R,6R)-3,4,5-triacetoxy-6-(acetoxymethyl)tetrahydro-2H-pyran-2-yl)acetic acid

: 603129-44-8
methyl 3,7-anhydro-4,5,6-tri-O-benzyl-2-deoxy-8-O-mesyl-D-gulo-D-glycero-octulonate

Guidance literature:: Multi-step reaction with 6 steps

1: 83 percent / DIC; DMAP / CH₂Cl₂ / 3 h / 20 °C

2: NaOMe / methanol / 2 h

3: 85 percent / pyridine / 16 h

4: 88 percent / NaH / dimethylformamide / 16 h

5: 100 percent / pTsOH / methanol; CH₂Cl₂

6: 100 percent / pyridine / 16 h

With dmap; sodium methylate; sodium hydride; toluene-4-sulfonic acid; dacarbazine; In pyridine; methanol; dichloromethane; N,N-dimethyl-formamide; 2: Zemplen deacylation;
DOI:10.1002/ejoc.200300031

Reference yield:

: 77838-27-8
methyl 4,5,6,8-tetra-O-acetyl-3,7-anhydro-2-deoxy-D-glycero-D-gulo-octulonate

: 603129-44-8
methyl 3,7-anhydro-4,5,6-tri-O-benzyl-2-deoxy-8-O-mesyl-D-gulo-D-glycero-octulonate

Guidance literature:: Multi-step reaction with 5 steps

1: NaOMe / methanol / 2 h

2: 85 percent / pyridine / 16 h

3: 88 percent / NaH / dimethylformamide / 16 h

4: 100 percent / pTsOH / methanol; CH₂Cl₂

5: 100 percent / pyridine / 16 h

With sodium methylate; sodium hydride; toluene-4-sulfonic acid; In pyridine; methanol; dichloromethane; N,N-dimethyl-formamide; 1: Zemplen deacylation;
DOI:10.1002/ejoc.200300031