2-O-benzyl-6-deoxy-6-iodo-3,4:5,6-bis-O-(1-methyloethylidene)-D-glycero-D-gulo-hept-1-ose

Base Information

• Chemical Name: 2-O-benzyl-6-deoxy-6-iodo-3,4:5,6-bis-O-(1-methyloethylidene)-D-glycero-D-gulo-hept-1-ose
• CAS No.: 408498-12-4
• Molecular Formula: C₂₀H₂₇IO₆
• Molecular Weight: 490.335

Synonyms:2-O-benzyl-6-deoxy-6-iodo-3,4:5,6-bis-O-(1-methyloethylidene)-D-glycero-D-gulo-hept-1-ose

Chemical Property of 2-O-benzyl-6-deoxy-6-iodo-3,4:5,6-bis-O-(1-methyloethylidene)-D-glycero-D-gulo-hept-1-ose

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Technology Process of 2-O-benzyl-6-deoxy-6-iodo-3,4:5,6-bis-O-(1-methyloethylidene)-D-glycero-D-gulo-hept-1-ose

There total 1 articles about 2-O-benzyl-6-deoxy-6-iodo-3,4:5,6-bis-O-(1-methyloethylidene)-D-glycero-D-gulo-hept-1-ose 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: 50.0%

1-O-benzyl-6-deoxy-6-iodo-2,3:4,5-bis-O-(1-methylethylidene)-1-(2-thiazolyl)-D-glycero-D-gulo-hexitol (354137-27-2) → 2-O-benzyl-6-deoxy-6-iodo-3,4:5,6-bis-O-(1-methyloethylidene)-D-glycero-D-gulo-hept-1-ose (408498-12-4) + benzyl 6-deoxy-6-iodo-2,3:4,5-bis-O-isopropylidene-D-gluconoate

Guidance literature:

1-O-benzyl-6-deoxy-6-iodo-2,3:4,5-bis-O-(1-methylethylidene)-1-(2-thiazolyl)-D-glycero-D-gulo-hexitol; With methyl iodide; In acetonitrile; at 80 ℃; for 24h;

With sodium tetrahydroborate; In methanol; at 0 ℃; for 0.5h;

With mercury dichloride; In water; acetonitrile; at 20 ℃; for 0.25h;

DOI:10.1081/CAR-100108278

Reference yield: 73.0%

methyl (triphenylphosphoranylidene)acetate (21204-67-1,2605-67-6) + 2-O-benzyl-6-deoxy-6-iodo-3,4:5,6-bis-O-(1-methyloethylidene)-D-glycero-D-gulo-hept-1-ose (408498-12-4) → (Z)-(S)-4-Benzyloxy-4-((4R,5S,4'S,5'S)-5'-iodomethyl-2,2,2',2'-tetramethyl-[4,4']bi[[1,3]dioxolanyl]-5-yl)-but-2-enoic acid methyl ester + (E)-(S)-4-Benzyloxy-4-((4R,5S,4'S,5'S)-5'-iodomethyl-2,2,2',2'-tetramethyl-[4,4']bi[[1,3]dioxolanyl]-5-yl)-but-2-enoic acid methyl ester

Guidance literature:

In dichloromethane; at 20 ℃;

DOI:10.1021/jo0111107

Reference yield: 56.0%

O-benzylhydoxylamine hydrochloride (2687-43-6) + 2-O-benzyl-6-deoxy-6-iodo-3,4:5,6-bis-O-(1-methyloethylidene)-D-glycero-D-gulo-hept-1-ose (408498-12-4) → (S)-Benzyloxy-((4R,5S,4'S,5'S)-5'-iodomethyl-2,2,2',2'-tetramethyl-[4,4']bi[[1,3]dioxolanyl]-5-yl)-acetaldehyde O-benzyl-oxime + (S)-Benzyloxy-((4R,5S,4'S,5'S)-5'-iodomethyl-2,2,2',2'-tetramethyl-[4,4']bi[[1,3]dioxolanyl]-5-yl)-acetaldehyde O-benzyl-oxime

Guidance literature:

With pyridine; at 20 ℃;

DOI:10.1021/jo0111107

upstream raw materials:

1-O-benzyl-6-deoxy-6-iodo-2,3:4,5-bis-O-(1-methylethylidene)-1-(2-thiazolyl)-D-glycero-D-gulo-hexitol

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