methyl 4-O-acetyl-2-O-benzoyl-6-deoxy-α-D-xylo-hexopyranosid-3-ulose (p-tolylsulfonyl)hydrazone

Base Information

Chemical Name:methyl 4-O-acetyl-2-O-benzoyl-6-deoxy-α-D-xylo-hexopyranosid-3-ulose (p-tolylsulfonyl)hydrazone
CAS No.:123076-90-4
Molecular Formula:C₂₃H₂₆N₂O₈S
Molecular Weight:490.534
Hs Code.:

Synonyms:methyl 4-O-acetyl-2-O-benzoyl-6-deoxy-α-D-xylo-hexopyranosid-3-ulose (p-tolylsulfonyl)hydrazone

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Chemical Property of methyl 4-O-acetyl-2-O-benzoyl-6-deoxy-α-D-xylo-hexopyranosid-3-ulose (p-tolylsulfonyl)hydrazone

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Technology Process of methyl 4-O-acetyl-2-O-benzoyl-6-deoxy-α-D-xylo-hexopyranosid-3-ulose (p-tolylsulfonyl)hydrazone

There total 6 articles about methyl 4-O-acetyl-2-O-benzoyl-6-deoxy-α-D-xylo-hexopyranosid-3-ulose (p-tolylsulfonyl)hydrazone 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: 82.0%

: 123076-88-0
methyl 4-O-acetyl-2-O-benzoyl-6-deoxy-α-D-xylo-hexopyranosid-3-ulose

: 1576-35-8
toluene-4-sulfonic acid hydrazide

: 123076-90-4
methyl 4-O-acetyl-2-O-benzoyl-6-deoxy-α-D-xylo-hexopyranosid-3-ulose (p-tolylsulfonyl)hydrazone

Guidance literature:: In methanol; for 12h; Ambient temperature;
DOI:10.1021/jo00278a035

Reference yield:

: 14917-69-2,17014-02-7,24577-96-6,39981-26-5,63848-11-3,65310-01-2,71772-35-5,72904-81-5,124264-65-9,135029-35-5
methyl 6-deoxy-3,4-O-isopropylidene-D-galactopyranoside

: 123076-90-4
methyl 4-O-acetyl-2-O-benzoyl-6-deoxy-α-D-xylo-hexopyranosid-3-ulose (p-tolylsulfonyl)hydrazone

Guidance literature:: Multi-step reaction with 5 steps

1: pyridine / 1.5 h / Ambient temperature

2: conc. aq. HCl / methanol / 0.75 h / Ambient temperature

3: 1.) p-toluenesulfonic acid, 2.) 80 percent acetic acid / 1.) methylene chloride, 12 h, RT, 2.) 15 min., RT

4: 89 percent / pyridinium chlorochromate, sodium acetate, molec. sieves 3-A / CH₂Cl₂ / 3 h / 0 - 20 °C

5: 82 percent / methanol / 12 h / Ambient temperature

With pyridine; hydrogenchloride; 3 A molecular sieve; sodium acetate; toluene-4-sulfonic acid; acetic acid; pyridinium chlorochromate; In methanol; dichloromethane;
DOI:10.1021/jo00278a035

Reference yield:

: 65222-57-3,78391-93-2,123163-96-2,143900-49-6,123163-95-1
methyl 2-O-benzoyl-6-deoxy-α-D-galactopyranoside

: 123076-90-4
methyl 4-O-acetyl-2-O-benzoyl-6-deoxy-α-D-xylo-hexopyranosid-3-ulose (p-tolylsulfonyl)hydrazone

Guidance literature:: Multi-step reaction with 3 steps

1: 1.) p-toluenesulfonic acid, 2.) 80 percent acetic acid / 1.) methylene chloride, 12 h, RT, 2.) 15 min., RT

2: 89 percent / pyridinium chlorochromate, sodium acetate, molec. sieves 3-A / CH₂Cl₂ / 3 h / 0 - 20 °C

3: 82 percent / methanol / 12 h / Ambient temperature

With 3 A molecular sieve; sodium acetate; toluene-4-sulfonic acid; acetic acid; pyridinium chlorochromate; In methanol; dichloromethane;
DOI:10.1021/jo00278a035