(Z)-(6-²H₁)-3-O-benzyl-5,6-dideoxy-1,2-isopropylidene-α-D-xylo-hex-5-enofuranose

Base Information

• Chemical Name: (Z)-(6-²H₁)-3-O-benzyl-5,6-dideoxy-1,2-isopropylidene-α-D-xylo-hex-5-enofuranose
• CAS No.: 93170-77-5
• Molecular Formula: C₁₆H₂₀O₄
• Molecular Weight: 277.324

Synonyms:(Z)-(6-²H₁)-3-O-benzyl-5,6-dideoxy-1,2-isopropylidene-α-D-xylo-hex-5-enofuranose

Chemical Property of (Z)-(6-²H₁)-3-O-benzyl-5,6-dideoxy-1,2-isopropylidene-α-D-xylo-hex-5-enofuranose

Chemical Property:

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Technology Process of (Z)-(6-²H₁)-3-O-benzyl-5,6-dideoxy-1,2-isopropylidene-α-D-xylo-hex-5-enofuranose

There total 4 articles about (Z)-(6-²H₁)-3-O-benzyl-5,6-dideoxy-1,2-isopropylidene-α-D-xylo-hex-5-enofuranose 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: 97.0%

(6-2H)-3-O-benzyl-5,6-dideoxy-1,2-O-isopropylidene-α-D-xylo-hex-5-yno-furanose (66108-68-7) → (Z)-(6-2H1)-3-O-benzyl-5,6-dideoxy-1,2-isopropylidene-α-D-xylo-hex-5-enofuranose (93170-77-5)

Guidance literature:

With quinoline; hydrogen; Lindlar's catalyst; In acetone;

DOI:10.1016/S0040-4020(01)88450-7

Reference yield:

O-benzyl-3-dibromo-6,6-didesoxy-5,6-O-isopropylidene-1,2-α-D-xylo-hexeno-5-furannose-1,4 (53931-26-3) → (Z)-(6-2H1)-3-O-benzyl-5,6-dideoxy-1,2-isopropylidene-α-D-xylo-hex-5-enofuranose (93170-77-5)

Guidance literature:

Multi-step reaction with 2 steps

1: 52 percent / n-butyllithium, deuterium oxide / tetrahydrofuran; hexane / -70 deg C, 3 h. then room temp, 1 h. (one-pot)

2: potassium azodicarboxylate, acetic acide / methanol / 21 h / Ambient temperature

With n-butyllithium; water-d2; potassium diazodicarboxylate; acetic acid; In tetrahydrofuran; methanol; hexane;

DOI:10.1016/S0040-4020(01)88450-7

Reference yield:

3-O-benzyl-1,2-O-isopropylidene-1,5-D-xylo-dialdofuranose (23558-05-6) → (Z)-(6-2H1)-3-O-benzyl-5,6-dideoxy-1,2-isopropylidene-α-D-xylo-hex-5-enofuranose (93170-77-5)

Guidance literature:

Multi-step reaction with 3 steps

1: 73 percent / triphenylphosphine / CH₂Cl₂ / 0 deg C, 30 min. then room temp., 1.5 h.

2: 52 percent / n-butyllithium, deuterium oxide / tetrahydrofuran; hexane / -70 deg C, 3 h. then room temp, 1 h. (one-pot)

3: potassium azodicarboxylate, acetic acide / methanol / 21 h / Ambient temperature

With n-butyllithium; water-d2; potassium diazodicarboxylate; acetic acid; triphenylphosphine; In tetrahydrofuran; methanol; hexane; dichloromethane;

DOI:10.1016/S0040-4020(01)88450-7

upstream raw materials:

(6-²H)-3-O-benzyl-5,6-dideoxy-1,2-O-isopropylidene-α-D-xylo-hex-5-yno-furanose

O-benzyl-3-dibromo-6,6-didesoxy-5,6-O-isopropylidene-1,2-α-D-xylo-hexeno-5-furannose-1,4

3-O-benzyl-1,2-O-isopropylidene-1,5-D-xylo-dialdofuranose

Downstream raw materials:

(6R)-(6-²H₁)-3-O-benzyl-1,2-O-isopropylidene-α-D-glucofuranose

(6R)-(6-²H₁)-5,6-O-diacetyl-3-O-benzyl-1,2-O-isopropylidene-α-D-glucofuranose

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