5,5a-didehydro-2,3,4,6-tetra-O-(ethoxymethyl)-5a-carba-α-D-xylohexopyranose

Base Information

• Chemical Name: 5,5a-didehydro-2,3,4,6-tetra-O-(ethoxymethyl)-5a-carba-α-D-xylohexopyranose
• CAS No.: 1323271-65-3
• Molecular Formula: C₁₉H₃₆O₉
• Molecular Weight: 408.489
• Mol file: 1323271-65-3.mol

Synonyms:5,5a-didehydro-2,3,4,6-tetra-O-(ethoxymethyl)-5a-carba-α-D-xylohexopyranose

Chemical Property of 5,5a-didehydro-2,3,4,6-tetra-O-(ethoxymethyl)-5a-carba-α-D-xylohexopyranose

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 5,5a-didehydro-2,3,4,6-tetra-O-(ethoxymethyl)-5a-carba-α-D-xylohexopyranose

There total 6 articles about 5,5a-didehydro-2,3,4,6-tetra-O-(ethoxymethyl)-5a-carba-α-D-xylohexopyranose 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: 86.0%

C19H34O9 (1323271-61-9) → C19H36O9 (1323271-67-5) + 5,5a-didehydro-2,3,4,6-tetra-O-(ethoxymethyl)-5a-carba-α-D-xylohexopyranose (1323271-65-3)

Guidance literature:

With potassium tri-sec-butyl-borohydride; In tetrahydrofuran; at -78 - 20 ℃; stereoselective reaction;

DOI:10.1055/s-0030-1260547

Reference yield: 75.0%

C19H34O9 (1323271-61-9) → 5,5a-didehydro-2,3,4,6-tetra-O-(ethoxymethyl)-5a-carba-α-D-xylohexopyranose (1323271-65-3)

Guidance literature:

With lithium triethylborohydride; In tetrahydrofuran; at -78 ℃; for 1.5h; Inert atmosphere;

Reference yield:

C21H43O13P → 5,5a-didehydro-2,3,4,6-tetra-O-(ethoxymethyl)-5a-carba-α-D-xylohexopyranose (1323271-65-3)

Guidance literature:

Multi-step reaction with 3 steps

1.1: sodium tetrahydroborate / methanol / 0.5 h / 20 °C

2.1: dimethyl sulfoxide; trifluoroacetic anhydride / dichloromethane / 5 h / -78 °C / Molecular sieve; Inert atmosphere

2.2: -78 - 20 °C / Inert atmosphere

3.1: cerium(III) chloride heptahydrate / methanol / 1 h / -20 °C

3.2: -20 °C

With sodium tetrahydroborate; cerium(III) chloride heptahydrate; dimethyl sulfoxide; trifluoroacetic anhydride; In methanol; dichloromethane;

DOI:10.1055/s-0030-1260547

upstream raw materials:

C₁₉H₃₄O₉

C₁₈H₃₄O₁₀

D-Glucono-1,5-lactone

Downstream raw materials:

7-O-acetyl-streptol

C₁₉H₃₈O₉

(1S)-(+)-(1,3/2,4,5)-2,3,4,5-tetrahydroxycyclohexanemethanol

α-valienol