methyl 3,7-anhydro-4,5,6-tri-O-benzyl-8-[(tert-butoxycarbonyl)-amino]-2,8-dideoxy-D-gulo-D-glycero-octulonate

Base Information

Chemical Name:methyl 3,7-anhydro-4,5,6-tri-O-benzyl-8-[(tert-butoxycarbonyl)-amino]-2,8-dideoxy-D-gulo-D-glycero-octulonate
CAS No.:603129-45-9
Molecular Formula:C₃₅H₄₃NO₈
Molecular Weight:605.728
Hs Code.:

Synonyms:methyl 3,7-anhydro-4,5,6-tri-O-benzyl-8-[(tert-butoxycarbonyl)-amino]-2,8-dideoxy-D-gulo-D-glycero-octulonate

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Chemical Property of methyl 3,7-anhydro-4,5,6-tri-O-benzyl-8-[(tert-butoxycarbonyl)-amino]-2,8-dideoxy-D-gulo-D-glycero-octulonate

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Technology Process of methyl 3,7-anhydro-4,5,6-tri-O-benzyl-8-[(tert-butoxycarbonyl)-amino]-2,8-dideoxy-D-gulo-D-glycero-octulonate

There total 8 articles about methyl 3,7-anhydro-4,5,6-tri-O-benzyl-8-[(tert-butoxycarbonyl)-amino]-2,8-dideoxy-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: 95.0%

: 74651-77-7
2-(tert-butoxycarbonyloxyimino)-2-phenylacetonitrile

: 497226-96-7
methyl 3,7-anhydro-8-azido-4,5,6-tri-O-benzyl-2,8-dideoxy-D-gulo-D-glycero-octulonate

: 603129-45-9
methyl 3,7-anhydro-4,5,6-tri-O-benzyl-8-[(tert-butoxycarbonyl)-amino]-2,8-dideoxy-D-gulo-D-glycero-octulonate

Guidance literature:: With trimethylphosphane; In toluene; at 20 ℃; for 5h;
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

: 603129-45-9
methyl 3,7-anhydro-4,5,6-tri-O-benzyl-8-[(tert-butoxycarbonyl)-amino]-2,8-dideoxy-D-gulo-D-glycero-octulonate

Guidance literature:: Multi-step reaction with 8 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

7: 77 percent / NaN₃ / dimethylformamide / 1.5 h / 75 °C

8: 95 percent / Me₃P / toluene / 5 h / 20 °C

With dmap; sodium azide; sodium methylate; sodium hydride; toluene-4-sulfonic acid; dacarbazine; trimethylphosphane; In pyridine; methanol; dichloromethane; N,N-dimethyl-formamide; toluene; 2: Zemplen deacylation / 8: modified Staudinger reaction;
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

: 603129-45-9
methyl 3,7-anhydro-4,5,6-tri-O-benzyl-8-[(tert-butoxycarbonyl)-amino]-2,8-dideoxy-D-gulo-D-glycero-octulonate

Guidance literature:: Multi-step reaction with 7 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

6: 77 percent / NaN₃ / dimethylformamide / 1.5 h / 75 °C

7: 95 percent / Me₃P / toluene / 5 h / 20 °C

With sodium azide; sodium methylate; sodium hydride; toluene-4-sulfonic acid; trimethylphosphane; In pyridine; methanol; dichloromethane; N,N-dimethyl-formamide; toluene; 1: Zemplen deacylation / 7: modified Staudinger reaction;
DOI:10.1002/ejoc.200300031