1,2-O-isopropylidene-3-C-(p-tolylsulfonyloxymethyl)-β-L-threo-tetrofuranose

Base Information

• Chemical Name: 1,2-O-isopropylidene-3-C-(p-tolylsulfonyloxymethyl)-β-L-threo-tetrofuranose
• CAS No.: 24738-21-4
• Molecular Formula: C₁₅H₂₀O₇S
• Molecular Weight: 344.386

Synonyms:1,2-O-isopropylidene-3-C-(p-tolylsulfonyloxymethyl)-β-L-threo-tetrofuranose

Chemical Property of 1,2-O-isopropylidene-3-C-(p-tolylsulfonyloxymethyl)-β-L-threo-tetrofuranose

Chemical Property:

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Technology Process of 1,2-O-isopropylidene-3-C-(p-tolylsulfonyloxymethyl)-β-L-threo-tetrofuranose

There total 3 articles about 1,2-O-isopropylidene-3-C-(p-tolylsulfonyloxymethyl)-β-L-threo-tetrofuranose 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: 78.0%

(-)-(3aR,6S,6aR)-6-hydroxymethyl-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-6-ol (14048-35-2) + p-toluenesulfonyl chloride (98-59-9) → 1,2-O-isopropylidene-3-C-(p-tolylsulfonyloxymethyl)-β-L-threo-tetrofuranose (24738-21-4)

Guidance literature:

With pyridine; at 25 ℃;

DOI:10.1016/0008-6215(84)85201-5

Reference yield:

1,2;3,3'-di-O-isopropylidene-3-C-(hydroxymethyl)-α-D-erythrofuranose (34724-16-8) → 1,2-O-isopropylidene-3-C-(p-tolylsulfonyloxymethyl)-β-L-threo-tetrofuranose (24738-21-4)

Guidance literature:

Multi-step reaction with 2 steps

1: 70 percent / 60 percent aqu. acetic acid / 60 h / Ambient temperature

2: 78 percent / pyridine / 25 °C

With pyridine; acetic acid;

DOI:10.1016/0008-6215(84)85201-5

Reference yield:

→ 1,2-O-isopropylidene-3-C-(p-tolylsulfonyloxymethyl)-β-L-threo-tetrofuranose (24738-21-4)

Guidance literature:

O¹,O²-Isopropyliden-α-D-apio-L-furanose, Toluol-4-sulfonylchlorid;

DOI:10.1016/S0008-6215(00)82246-6

upstream raw materials:

(-)-(3aR,6S,6aR)-6-hydroxymethyl-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-6-ol

p-toluenesulfonyl chloride

1,2;3,3'-di-O-isopropylidene-3-C-(hydroxymethyl)-α-D-erythrofuranose

Downstream raw materials:

(2S,3S)-2-methylbutane-1,2,3,4-tetraol

1,2,3,4-tetra-O-benzoyl-3-C-methyl-L-threitol

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