(2S,3R,4R)-Hex-5-ene-1,2,3,4-tetraol

Base Information

• Chemical Name: (2S,3R,4R)-Hex-5-ene-1,2,3,4-tetraol
• CAS No.: 201800-16-0
• Molecular Formula: C₆H₁₂O₄
• Molecular Weight: 148.159

Synonyms:

Chemical Property of (2S,3R,4R)-Hex-5-ene-1,2,3,4-tetraol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
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Technology Process of (2S,3R,4R)-Hex-5-ene-1,2,3,4-tetraol

There total 10 articles about (2S,3R,4R)-Hex-5-ene-1,2,3,4-tetraol 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:

(2S,3R,4S,5R)-5-Vinyl-tetrahydro-furan-2,3,4-triol → (2S,3R,4R)-Hex-5-ene-1,2,3,4-tetraol (201800-16-0)

Guidance literature:

With sodium tetrahydroborate; In tetrahydrofuran; water; for 2h; Yield given; Ambient temperature;

DOI:10.1002/hlca.19970800803

Reference yield:

(1,2:5,6)-di-O-isopropylidene-D-gulose (14686-89-6) → (2S,3R,4R)-Hex-5-ene-1,2,3,4-tetraol (201800-16-0)

Guidance literature:

Multi-step reaction with 7 steps

1: DMAP / CH₂Cl₂; pyridine / 1 h / Ambient temperature

2: AcOH, HCOOH / H₂O / 1 h / Ambient temperature

3: Et₃N / CH₂Cl₂ / 0.33 h / 4 °C

4: NaI / various solvent(s) / 2.5 h / 100 °C

5: 10N aq. NaOH / methanol / 0.5 h / Ambient temperature

6: resin IR 120 (H⁺ form) / tetrahydrofuran; H₂O / 3.5 h / 80 °C

7: NaBH₄ / tetrahydrofuran; H₂O / 2 h / Ambient temperature

With dmap; sodium hydroxide; sodium tetrahydroborate; formic acid; resin IR 120 (H⁺ form); acetic acid; triethylamine; sodium iodide; In tetrahydrofuran; pyridine; methanol; dichloromethane; water;

DOI:10.1002/hlca.19970800803

Reference yield:

1,2:5,6-di-O-isopropylidene-α-D-hexofuran-3-ulose (2847-00-9) → (2S,3R,4R)-Hex-5-ene-1,2,3,4-tetraol (201800-16-0)

Guidance literature:

Multi-step reaction with 8 steps

1: NaBH₄ / ethanol; H₂O / 3 h / Ambient temperature

2: DMAP / CH₂Cl₂; pyridine / 1 h / Ambient temperature

3: AcOH, HCOOH / H₂O / 1 h / Ambient temperature

4: Et₃N / CH₂Cl₂ / 0.33 h / 4 °C

5: NaI / various solvent(s) / 2.5 h / 100 °C

6: 10N aq. NaOH / methanol / 0.5 h / Ambient temperature

7: resin IR 120 (H⁺ form) / tetrahydrofuran; H₂O / 3.5 h / 80 °C

8: NaBH₄ / tetrahydrofuran; H₂O / 2 h / Ambient temperature

With dmap; sodium hydroxide; sodium tetrahydroborate; formic acid; resin IR 120 (H⁺ form); acetic acid; triethylamine; sodium iodide; In tetrahydrofuran; pyridine; methanol; ethanol; dichloromethane; water;

DOI:10.1002/hlca.19970800803

upstream raw materials:

(1,2:5,6)-di-O-isopropylidene-D-gulose

1,2:5,6-di-O-isopropylidene-α-D-hexofuran-3-ulose

Benzoic acid (3aR,5R,6R,6aR)-2,2-dimethyl-5-vinyl-tetrahydro-furo[2,3-d][1,3]dioxol-6-yl ester

5,6-dideoxy-1,2-O-isopropylidene-α-D-allo-hex-5-endofuranoside

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