dibenzyl 2-O-acetyl-3,4,6-trideoxy-4-C-difluoromethylene-α-D-erythro-hexopyranosyl phosphate

Base Information

Chemical Name:dibenzyl 2-O-acetyl-3,4,6-trideoxy-4-C-difluoromethylene-α-D-erythro-hexopyranosyl phosphate
CAS No.:371229-01-5
Molecular Formula:C₂₃H₂₅F₂O₇P
Molecular Weight:482.418
Hs Code.:

Synonyms:dibenzyl 2-O-acetyl-3,4,6-trideoxy-4-C-difluoromethylene-α-D-erythro-hexopyranosyl phosphate

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Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

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Chemical Property of dibenzyl 2-O-acetyl-3,4,6-trideoxy-4-C-difluoromethylene-α-D-erythro-hexopyranosyl phosphate

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Technology Process of dibenzyl 2-O-acetyl-3,4,6-trideoxy-4-C-difluoromethylene-α-D-erythro-hexopyranosyl phosphate

There total 11 articles about dibenzyl 2-O-acetyl-3,4,6-trideoxy-4-C-difluoromethylene-α-D-erythro-hexopyranosyl phosphate 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: 74.0%

: 538-37-4
dibenzyl phosphochloridate

: 1025968-85-7
Acetic acid (3R,6R)-5-difluoromethylene-2-hydroxy-6-methyl-tetrahydro-pyran-3-yl ester

: 371229-01-5
dibenzyl 2-O-acetyl-3,4,6-trideoxy-4-C-difluoromethylene-α-D-erythro-hexopyranosyl phosphate

Guidance literature:: With n-butyllithium; In tetrahydrofuran; hexane; at -78 - 0 ℃; for 2h;
DOI:10.1021/jo0103672

Reference yield:

: 31899-66-8
methyl 3,6-dideoxy-α-D-ribo-hexapyranoside

: 371229-01-5
dibenzyl 2-O-acetyl-3,4,6-trideoxy-4-C-difluoromethylene-α-D-erythro-hexopyranosyl phosphate

Guidance literature:: Multi-step reaction with 8 steps

1: 91 percent / pyridine / 2 h / 0 °C

2: 81 percent / sodium acetate; PCC / CH₂Cl₂ / 12 h / 20 °C

3: 86 percent / hexamethylphosphorus triamide / tetrahydrofuran / 2 h / 20 °C

4: 93 percent / potassium hydroxide / methanol / 2 h / 20 °C

5: Dowex 50WX₄-200 cation resin (H⁺ type) / H₂O; acetonitrile / 12 h / 50 °C

6: 0.37 g / pyridine / 2.5 h / 0 °C

7: 63 percent / tributyltin methoxide / CH₂Cl₂ / 37 h / Heating

8: 74 percent / n-BuLi / tetrahydrofuran; hexane / 2 h / -78 - 0 °C

With pyridine; N,N,N,N,N,N-hexamethylphosphoric triamide; potassium hydroxide; n-butyllithium; Dowex 50WX₄-200 cation resin (H⁺ type); sodium acetate; tributyltin methoxide; pyridinium chlorochromate; In tetrahydrofuran; methanol; hexane; dichloromethane; water; acetonitrile; 3: Wittig-type reaction;
DOI:10.1021/jo0103672

Reference yield:

: 17176-77-1
Dibenzyl phosphite

: 371229-01-5
dibenzyl 2-O-acetyl-3,4,6-trideoxy-4-C-difluoromethylene-α-D-erythro-hexopyranosyl phosphate

Guidance literature:: Multi-step reaction with 2 steps

1: NCS / benzene

2: 74 percent / n-BuLi / tetrahydrofuran; hexane / 2 h / -78 - 0 °C

With N-chloro-succinimide; n-butyllithium; In tetrahydrofuran; hexane; benzene;
DOI:10.1021/jo0103672