D-arabino-Hexitol, 1,5-anhydro-2-deoxy-4,6-O-[(R)-phenylmethylene]-, benzoate

Base Information

• Chemical Name: D-arabino-Hexitol, 1,5-anhydro-2-deoxy-4,6-O-[(R)-phenylmethylene]-, benzoate
• CAS No.: 438216-14-9
• Molecular Formula: C₂₀H₂₀O₅
• Molecular Weight: 340.376
• DSSTox Substance ID: DTXSID701140113
• Mol file: 438216-14-9.mol

Synonyms:DTXSID701140113;D-arabino-Hexitol, 1,5-anhydro-2-deoxy-4,6-O-[(R)-phenylmethylene]-, benzoate;438216-14-9

Chemical Property of D-arabino-Hexitol, 1,5-anhydro-2-deoxy-4,6-O-[(R)-phenylmethylene]-, benzoate

Chemical Property:

• XLogP3: 3.1
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 4
• Exact Mass: 340.13107373
• Heavy Atom Count: 25
• Complexity: 441

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: C1COC2COC(OC2C1OC(=O)C3=CC=CC=C3)C4=CC=CC=C4
• Isomeric SMILES: C1CO[C@@H]2CO[C@H](O[C@H]2[C@@H]1OC(=O)C3=CC=CC=C3)C4=CC=CC=C4

Technology Process of D-arabino-Hexitol, 1,5-anhydro-2-deoxy-4,6-O-[(R)-phenylmethylene]-, benzoate

There total 1 articles about D-arabino-Hexitol, 1,5-anhydro-2-deoxy-4,6-O-[(R)-phenylmethylene]-, benzoate 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%

1,5-Anhydro-2-deoxy-4,6-O-(phenylmethylene)-D-arabino-hexopyranoside (135214-83-4) + benzoyl chloride (98-88-4) → 3-O-benzoyl-4,6-O-benzylidene-1,2-dideoxy-D-glucopyranose (438216-14-9)

Guidance literature:

With dmap; triethylamine; In dichloromethane; at 20 ℃; for 2h;

DOI:10.1021/jo0110956

Reference yield: 92.0%

3-O-benzoyl-4,6-O-benzylidene-1,2-dideoxy-D-glucopyranose (438216-14-9) → 3-O-benzoyl-6-O-benzyl-1,2-dideoxy-D-glucopyranose (438216-15-0)

Guidance literature:

With hydrogenchloride; 4 A molecular sieve; sodium cyanoborohydride; In tetrahydrofuran; diethyl ether; at 20 ℃;

DOI:10.1021/jo0110956

Reference yield:

3-O-benzoyl-4,6-O-benzylidene-1,2-dideoxy-D-glucopyranose (438216-14-9) → (3-O-[(S)-1-(oxycarbonyl)-2-cyclohexylethyloxy]-β-D-galactopyranosyl-O-(1->3)-[α-L-fucopyranosyl)-O-(1->4)]-1,2-dideoxy-D-glucopyranose

Guidance literature:

Multi-step reaction with 7 steps

1.1: 92 percent / NaBH₃CN; HCl; 4 Angstroem molecular sieves / diethyl ether; tetrahydrofuran / 20 °C

2.1: 1,1,3,3-tetramethylurea; 4 Angsroem molecular sieves / CH₂Cl₂ / 20 °C

2.2: AgOTf / CH₂Cl₂ / 24 h / 20 °C

3.1: 85 percent / NaOMe / methanol / 2 h / 45 °C

4.1: NaH / tetrahydrofuran / 0.5 h / 0 °C

4.2: 48 percent / AgOTf; 4 Angstroem molecular sieves / CH₂Cl₂ / 0 - 20 °C

5.1: aq. LiOH / tetrahydrofuran / 48 h / 20 °C

6.1: 90 percent / NaOme / methanol / 2 h / Heating

7.1: H₂; AcOH / Pd(OH)2/C / dioxane / 40 h / 20 °C

With hydrogenchloride; lithium hydroxide; 4 A molecular sieve; hydrogen; sodium methylate; sodium hydride; sodium cyanoborohydride; acetic acid; tetramethylurea; palladium dihydroxide; In tetrahydrofuran; 1,4-dioxane; methanol; diethyl ether; dichloromethane;

DOI:10.1021/jo0110956

upstream raw materials:

1,5-Anhydro-2-deoxy-4,6-O-(phenylmethylene)-D-arabino-hexopyranoside

benzoyl chloride

Downstream raw materials:

3-O-benzoyl-6-O-benzyl-1,2-dideoxy-D-glucopyranose

(2,3,4-tri-O-benzyl-α-L-fucopyranosyl)-O-(1->4)-6-O-benzyl-1,2,-dideoxy-D-glucopyranose

(2,3,4-tri-O-benzyl-α-L-fucopyranosyl)-O-(1->4)-3-O-benzoyl-6-O-benzyl-1,2,-dideoxy-D-glucopyranose

(4,6-O-benzylidene-3-O-[(S)-1-(oxycarbonyl)-2-cyclohexylethyloxy]-β-D-galactopyranosyl-O-(1->3)-[(2,3,4-tri-O-benzyl-α-L-fucopyranosyl)-O-(1->4)]-6-O-benzyl-1,2-dideoxy-D-glucopyranose