3,6-di-O-acetyl-D-glucal

Base Information

• Chemical Name: 3,6-di-O-acetyl-D-glucal
• CAS No.: 63914-23-8
• Molecular Formula: C₁₀H₁₄O₆
• Molecular Weight: 230.218
• Mol file: 63914-23-8.mol

Synonyms:3,6-di-O-acetyl-D-glucal

Chemical Property of 3,6-di-O-acetyl-D-glucal

Chemical Property:

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 3,6-di-O-acetyl-D-glucal

There total 2 articles about 3,6-di-O-acetyl-D-glucal 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: 24.0%

D-glucal triacetate (2873-29-2) → 3,6-di-O-acetyl-D-glucal (63914-23-8) + 3,4-di-O-acetyl-1,5-anhydro-2-deoxy-D-arabino-hex-1-enitol (82295-98-5) + 4,6-di-O-acetyl-3-O-D-glucal (118356-98-2)

Guidance literature:

With lipase of Rhizopus oryze expressed in Pichia pastoris immobilized on octyl-Sepharose N-terminus modified by Boc-Ala-Gly-OH; In aq. phosphate buffer; at 25 ℃; for 24h; pH=4.8; Reagent/catalyst; Solvent; regioselective reaction; Catalytic behavior; Enzymatic reaction;

DOI:10.1039/c7cy00255f

Reference yield:

acetic anhydride (108-24-7) + D-glucal (13265-84-4) → 6-Monoacetylated D-glucal (63914-24-9) + 3,6-di-O-acetyl-D-glucal (63914-23-8) + 4,6-di-O-acetyl-3-O-D-glucal (118356-98-2) + D-glucal triacetate (2873-29-2)

Guidance literature:

With sodium bromide; In N,N-dimethyl-formamide; Yield given. Yields of byproduct given; Ambient temperature; electrolysis: Pt as working el., Ag/Ag(+) in CH₃CN as reference el.;

Reference yield:

3,6-di-O-acetyl-D-glucal (63914-23-8) → (2R,3S,4R)-4-Benzyloxy-2-benzyloxymethyl-3-((2R,4R,5R,6R)-4,5-bis-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxy)-3,4-dihydro-2H-pyran (686341-48-0)

Guidance literature:

Multi-step reaction with 2 steps

1.1: 92 percent / [ReOCl₃(SMe₂)(Ph₃PO)] / toluene / 6 h / 0 - 20 °C

2.1: NaOMe / methanol / 14 h / 0 - 20 °C

2.2: sodium hydride / dimethylformamide / 1.5 h / 0 °C

2.3: 67 percent / TBAI / dimethylformamide / 14 h / 20 °C

With [ReOCl₃(SMe₂)(Ph₃PO)]; sodium methylate; In methanol; toluene;

DOI:10.1021/ja031895t

upstream raw materials:

acetic anhydride

D-glucal

D-glucal triacetate

Downstream raw materials:

(2R,3S,4R)-4-Benzyloxy-2-benzyloxymethyl-3-((2R,4R,5R,6R)-4,5-bis-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxy)-3,4-dihydro-2H-pyran

(2R,3S,4R)-4-Benzyloxy-2-benzyloxymethyl-3-methoxymethoxy-3,4-dihydro-2H-pyran

(2R,4R)-4-Benzyloxy-2-benzyloxymethyl-6-methoxy-dihydro-pyran-3-one

(R)-2-((2R,3S,4S,6S,8S)-4,8-Bis-benzyloxy-2-ethyl-1,5-dioxa-spiro[2.5]oct-6-yl)-pentanal