2,6-anhydro-3,4,5,7-tetra-O-benzyl-1-deoxy-1-iodo-D-glycero-D-gulo-heptitol

Base Information

• Chemical Name: 2,6-anhydro-3,4,5,7-tetra-O-benzyl-1-deoxy-1-iodo-D-glycero-D-gulo-heptitol
• CAS No.: 246864-26-6
• Molecular Formula: C₃₅H₃₇IO₅
• Molecular Weight: 664.58

Synonyms:2,6-anhydro-3,4,5,7-tetra-O-benzyl-1-deoxy-1-iodo-D-glycero-D-gulo-heptitol

Chemical Property of 2,6-anhydro-3,4,5,7-tetra-O-benzyl-1-deoxy-1-iodo-D-glycero-D-gulo-heptitol

Chemical Property:

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Technology Process of 2,6-anhydro-3,4,5,7-tetra-O-benzyl-1-deoxy-1-iodo-D-glycero-D-gulo-heptitol

There total 2 articles about 2,6-anhydro-3,4,5,7-tetra-O-benzyl-1-deoxy-1-iodo-D-glycero-D-gulo-heptitol 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: 81.0%

β-C-(hydroxymethyl)-2,3,4,6-tetra-O-benzyl-β-D-glucopyranoside (89064-71-1) → 2,6-anhydro-3,4,5,7-tetra-O-benzyl-1-deoxy-1-iodo-D-glycero-D-gulo-heptitol (246864-26-6)

Guidance literature:

With 1H-imidazole; iodine; triphenylphosphine;

DOI:10.1002/(SICI)1521-3773(19991004)38:19<2939::AID-ANIE2939>3.0.CO;2-S

Reference yield:

2,6-anhydro-3,4,5,7-tetra-O-benzyl-1-deoxy-D-gluco-hept-1-enitol (133697-34-4,97321-70-5) → 2,6-anhydro-3,4,5,7-tetra-O-benzyl-1-deoxy-1-iodo-D-glycero-D-gulo-heptitol (246864-26-6)

Guidance literature:

Multi-step reaction with 2 steps

1.1: 9-BBN / tetrahydrofuran / 0 - 20 °C

1.2: H₂O₂; aq. KOH

2.1: 0.674 g / PPh₃; imidazole; I₂ / toluene / 0.5 h / 70 °C

With 1H-imidazole; 9-borabicyclo[3.3.1]nonane dimer; iodine; triphenylphosphine; In tetrahydrofuran; toluene;

DOI:10.1002/1099-0690(200204)2002:7<1323::AID-EJOC1323>3.0.CO;2-8

Reference yield: 72.0%

methyl 2,3,4-tri-O-benzyl-6-deoxy-6-mercapto-α-D-glucopyranoside (252851-40-4) + 2,6-anhydro-3,4,5,7-tetra-O-benzyl-1-deoxy-1-iodo-D-glycero-D-gulo-heptitol (246864-26-6) → methyl 2,3,4-tri-O-benzyl-6-S-(2',6'-anhydro-3',4',5',7'-tetra-O-benzyl-1'-deoxy-D-glycero-D-gulo-heptitol-1-yl)-6-thio-α-D-glucopyranoside (441044-63-9)

Guidance literature:

With potassium carbonate; In acetone; for 4h; Heating;

DOI:10.1002/1099-0690(200204)2002:7<1323::AID-EJOC1323>3.0.CO;2-8

upstream raw materials:

β-C-(hydroxymethyl)-2,3,4,6-tetra-O-benzyl-β-D-glucopyranoside

2,6-anhydro-3,4,5,7-tetra-O-benzyl-1-deoxy-D-gluco-hept-1-enitol

Downstream raw materials:

2,6-anhydro-3,4,5,7-tetra-O-benzyl-1-S-(2',3',4',6'-tetra-O-benzyl-β-D-glucopyranosyl)-1-thio-β-D-glycero-D-gulo-heptitol

(4S)-S-(2',6'-anhydro-3',4',5',7'-tetra-O-benzyl-1'-deoxy-D-glycero-D-gulo-heptitol-1'-yl)-N-(tert-butoxycarbonyl)-2,2-dimethyl-4-(thiomethyl)-1,3-oxazolidine

methyl 2,3,4-tri-O-benzyl-6-S-(2',6'-anhydro-3',4',5',7'-tetra-O-benzyl-1'-deoxy-D-glycero-D-gulo-heptitol-1-yl)-6-thio-α-D-glucopyranoside

(Z)-methyl 8,12-anhydro-2,3,4,9,10,11,13-hepta-O-benzyl-6,7-dideoxy-α-D-glycero-D-gulo-tridec-6-enopyranoside

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