5,6-dideoxy-1,2,3,4-di-O-isopropylidene-5-eno-L-lyxo-hexose-S-phenyl-monothiohemiacetal

Base Information

Chemical Name:5,6-dideoxy-1,2,3,4-di-O-isopropylidene-5-eno-L-lyxo-hexose-S-phenyl-monothiohemiacetal
CAS No.:904310-22-1
Molecular Formula:C₁₈H₂₄O₄S
Molecular Weight:336.452
Hs Code.:

Synonyms:5,6-dideoxy-1,2,3,4-di-O-isopropylidene-5-eno-L-lyxo-hexose-S-phenyl-monothiohemiacetal

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Chemical Property of 5,6-dideoxy-1,2,3,4-di-O-isopropylidene-5-eno-L-lyxo-hexose-S-phenyl-monothiohemiacetal

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Technology Process of 5,6-dideoxy-1,2,3,4-di-O-isopropylidene-5-eno-L-lyxo-hexose-S-phenyl-monothiohemiacetal

There total 6 articles about 5,6-dideoxy-1,2,3,4-di-O-isopropylidene-5-eno-L-lyxo-hexose-S-phenyl-monothiohemiacetal 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: 87.0%

: 904310-17-4
5,6-dideoxy-1,2-O-isopropylidene-5-eno-L-lyxo-hexose-S-phenyl-monothiohemiacetal

: 77-76-9
2,2-dimethoxy-propane

: 904310-22-1
5,6-dideoxy-1,2,3,4-di-O-isopropylidene-5-eno-L-lyxo-hexose-S-phenyl-monothiohemiacetal

Guidance literature:: With camphor-10-sulfonic acid; In dichloromethane; at 0 ℃; for 1h;
DOI:10.1016/j.carres.2006.04.026

Reference yield:

: 1,3-di-O-acetyl-4,5-dideoxy-1,2-O-isopropylidene-4-eno-L-threo-pentose

: 904310-22-1
5,6-dideoxy-1,2,3,4-di-O-isopropylidene-5-eno-L-lyxo-hexose-S-phenyl-monothiohemiacetal

Guidance literature:: Multi-step reaction with 5 steps

1.1: 88 percent / BF₃*OEt₂ / CH₂Cl₂ / 1 h / -78 - -40 °C

2.1: 99 percent / NaOCH₃ / methanol / 2 h / 20 °C

3.1: 98 percent / diisopropylazodicarboxylate; Ph₃P / toluene / 2 h / 0 °C

4.1: O₃ / CH₂Cl₂; methanol / -78 °C

4.2: Ph₃P / CH₂Cl₂; methanol / 1 h / 20 °C

4.3: tetrahydrofuran / 1 h / 0 °C

5.1: 87 percent / camphorsulfonic acid / CH₂Cl₂ / 1 h / 0 °C

With di-isopropyl azodicarboxylate; camphor-10-sulfonic acid; boron trifluoride diethyl etherate; sodium methylate; ozone; triphenylphosphine; In methanol; dichloromethane; toluene; 3.1: Mitsunobu reaction / 4.3: Grignard addition;
DOI:10.1016/j.carres.2006.04.026

Reference yield:

: 904310-57-2
(S)-1-((4R,5R)-2,2-Dimethyl-5-phenylsulfanyl-[1,3]dioxolan-4-yl)-prop-2-en-1-ol

: 904310-22-1
5,6-dideoxy-1,2,3,4-di-O-isopropylidene-5-eno-L-lyxo-hexose-S-phenyl-monothiohemiacetal

Guidance literature:: Multi-step reaction with 3 steps

1.1: 98 percent / diisopropylazodicarboxylate; Ph₃P / toluene / 2 h / 0 °C

2.1: O₃ / CH₂Cl₂; methanol / -78 °C

2.2: Ph₃P / CH₂Cl₂; methanol / 1 h / 20 °C

2.3: tetrahydrofuran / 1 h / 0 °C

3.1: 87 percent / camphorsulfonic acid / CH₂Cl₂ / 1 h / 0 °C

With di-isopropyl azodicarboxylate; camphor-10-sulfonic acid; ozone; triphenylphosphine; In methanol; dichloromethane; toluene; 1.1: Mitsunobu reaction / 2.3: Grignard addition;
DOI:10.1016/j.carres.2006.04.026