1,6-anhydro-2-deoxy-2-iodo-D-glucopyranose

Base Information

• Chemical Name: 1,6-anhydro-2-deoxy-2-iodo-D-glucopyranose
• CAS No.: 139437-39-1
• Molecular Formula: C6H9IO4
• Molecular Weight: 272.04
• Hs Code.: 2932990090
• Mol file: 139437-39-1.mol

Synonyms:1,6-anhydro-2-azido-3,4-di-O-benzyl-2-deoxy-D-glucopyranose;1,6-Anhydro-2,4-di-O-p-tolylsulfonyl-b-D-glucopyranose;2,4-di-O-tosyllevoglucosan;1,6-Anhydro-2,4-di-O-p-toluenesulfonyl-|A-D-glucopyranose;2-iodolevoglucosan;

Chemical Property of 1,6-anhydro-2-deoxy-2-iodo-D-glucopyranose

Chemical Property:

• Melting Point: 101℃
• PSA: 58.92000
• Density: 2.23
• LogP: -0.73310

Purity/Quality:

98%Min ^*data from raw suppliers

1,6-Anhydro-2-deoxy-2-iodo-b-D-glucopyranose ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 1,6-anhydro-2-deoxy-2-iodo-D-glucopyranose

There total 5 articles about 1,6-anhydro-2-deoxy-2-iodo-D-glucopyranose 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: 65.0%

D-glucal (13265-84-4) → 1,6-anhydro-2-deoxy-2-iodo-β-D-glucopyranose (139437-39-1)

Guidance literature:

D-glucal; With 3 Angstroem MS; bis(tri-n-butyltin)oxide; In acetonitrile; for 3h; Heating;

With iodine; In dichloromethane; at 0 ℃; for 0.25h; Further stages.;

DOI:10.1002/1099-0690(200206)2002:12<1925::AID-EJOC1925>3.0.CO;2-9

Reference yield:

D-glucal triacetate (2873-29-2) → 1,6-anhydro-2-deoxy-2-iodo-β-D-glucopyranose (139437-39-1)

Guidance literature:

Multi-step reaction with 2 steps

1: 98 percent / H₂O, NEt₃ / methanol

2: 1) (Bu₃Sn)2O, molecular sieves 3 Angstroem, 2) I₂ / 1) CH₃CN, 3 h, reflux, 2a) 5 deg C, 15 min, 2b) RT, 2 h

With 3 A molecular sieve; water; iodine; triethylamine; bis(tri-n-butyltin)oxide; In methanol;

DOI:10.1016/0008-6215(93)80026-B

Reference yield:

alpha-D-glucopyranose (492-62-6) → 1,6-anhydro-2-deoxy-2-iodo-β-D-glucopyranose (139437-39-1)

Guidance literature:

Multi-step reaction with 3 steps

1.1: sulfuric acid; acetic acid / 2.5 h / 0 - 75 °C / Industry scale

2.1: hydrogen bromide; acetic acid / 2 h / 20 °C / Industry scale

2.2: 2 h / 0 - 5 °C / Industry scale

3.1: sodium methylate / methanol / 5 - 20 °C / pH 9 - 9.5 / Industry scale

3.2: 5 h / Reflux; Molecular sieve; Industry scale

3.3: 0 - 20 °C

With hydrogen bromide; sodium methylate; acetic acid; sulfuric acid; acetic acid; In methanol;

upstream raw materials:

D-glucal

D-glucal triacetate

α-D-glucopyranose peracetylate

alpha-D-glucopyranose

Downstream raw materials:

1,6:2,3-bisanhydro-4-O-p-methoxybenzyl-β-D-glucopyranose

1,6-anhydro-2-azido-3-O-benzyl-2-deoxy-4-O-(p-methoxybenzyl)-β-D-glucopyranose

1,6-anhydro-2-azido-2-deoxy-4-O-p-methoxybenzyl-β-D-glucopyranose

2-O-allyl-1,6-anhydro-4-O-p-methoxybenzyl-β-D-glucopyranose

Refernces

• 1、 -. "AN EFFICIENT AND SCALABLE PROCESS FOR THE MANUFACTURE OF FONDAPARINUX SODIUM". Page/Page column 15; 23; 43; 44. . Retrieved 2013/08/15.
• 2、 -. "PROCESS FOR PREPARING HEPARINOIDS AND INTERMEDIATES USEFUL IN THE SYNTHESIS THEREOF". Page/Page column 15. . Retrieved 2013/02/28.