methyl 4-O-acetyl-2-O-benzoyl-3,6-dideoxy-3-<2-(p-tolylsulfonyl)hydrazino>-β-L-gulopyranoside

Base Information

• Chemical Name: methyl 4-O-acetyl-2-O-benzoyl-3,6-dideoxy-3-<2-(p-tolylsulfonyl)hydrazino>-β-L-gulopyranoside
• CAS No.: 123077-01-0
• Molecular Formula: C₂₃H₂₈N₂O₈S
• Molecular Weight: 492.55
• Mol file: 123077-01-0.mol

Synonyms:

Chemical Property of methyl 4-O-acetyl-2-O-benzoyl-3,6-dideoxy-3-<2-(p-tolylsulfonyl)hydrazino>-β-L-gulopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of methyl 4-O-acetyl-2-O-benzoyl-3,6-dideoxy-3-<2-(p-tolylsulfonyl)hydrazino>-β-L-gulopyranoside

There total 14 articles about methyl 4-O-acetyl-2-O-benzoyl-3,6-dideoxy-3-<2-(p-tolylsulfonyl)hydrazino>-β-L-gulopyranoside 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: 79.0%

methyl 4-O-acetyl-2-O-benzoyl-6-deoxy-α-D-xylo-hexopyranosid-3-ulose (p-tolylsulfonyl)hydrazone (123076-90-4) → methyl 4-O-acetyl-2-O-benzoyl-3,6-dideoxy-3-<2-(p-tolylsulfonyl)hydrazino>-α-D-gulopyranoside (113668-66-9,122948-62-3,123076-92-6,123076-93-7,123077-00-9,123077-01-0)

Guidance literature:

With hydrogenchloride; sodium cyanoborohydride; In tetrahydrofuran; methanol;

DOI:10.1021/jo00278a035

Reference yield:

(3S,4R,5S,6S)-2-methoxy-6-methyltetrahydro-2H-pyran-3,4,5-triol (65310-00-1) → methyl 4-O-acetyl-2-O-benzoyl-3,6-dideoxy-3-<2-(p-tolylsulfonyl)hydrazino>-β-L-gulopyranoside (123077-01-0)

Guidance literature:

Multi-step reaction with 6 steps

1: p-toluenosulfonic acid / CH₂Cl₂ / Ambient temperature

2: triethyl amine, 4-(dimethylamino)pyririne / CH₂Cl₂ / Heating

3: 80 percent aq. acetic acid / 0.5 h / Ambient temperature

4: 89 percent / pyridinum chlorochromate, sodium acetate, molec. sievesA-3 / CH₂Cl₂; diethyl ether / 3 h / 0 - 20 °C

5: 74 percent / ethanol / Heating

6: NaBH₃CN, 0.1 N HCl / tetrahydrofuran; methanol

With hydrogenchloride; dmap; 3 A molecular sieve; sodium acetate; sodium cyanoborohydride; toluene-4-sulfonic acid; acetic acid; triethylamine; pyridinium chlorochromate; In tetrahydrofuran; methanol; diethyl ether; ethanol; dichloromethane;

DOI:10.1021/jo00278a035

Reference yield:

methyl 6-deoxy-3,4-O-isopropylidene-D-galactopyranoside (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 4-O-acetyl-2-O-benzoyl-3,6-dideoxy-3-<2-(p-tolylsulfonyl)hydrazino>-α-D-gulopyranoside (113668-66-9,122948-62-3,123076-92-6,123076-93-7,123077-00-9,123077-01-0)

Guidance literature:

Multi-step reaction with 6 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

6: 79 percent / NaBH₃CN, 0.1 N HCl / tetrahydrofuran; methanol

With pyridine; hydrogenchloride; 3 A molecular sieve; sodium acetate; sodium cyanoborohydride; toluene-4-sulfonic acid; acetic acid; pyridinium chlorochromate; In tetrahydrofuran; methanol; dichloromethane;

DOI:10.1021/jo00278a035

upstream raw materials:

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

methyl 6-deoxy-3,4-O-isopropylidene-D-galactopyranoside

methyl 2-O-benzoyl-6-deoxy-α-D-galactopyranoside

methyl 2-O-benzoyl-6-deoxy-3,4-O-isopropylidene-α-D-galactopyranoside