(4S,6S)-4-(iodomethyl)-6-(((2R,6S)-6-(2-(4-methoxybenzyloxy)ethyl)-5,6-dihydro-2H-pyran-2-yl)methyl)-1,3-dioxan-2-one

Base Information

• Chemical Name: (4S,6S)-4-(iodomethyl)-6-(((2R,6S)-6-(2-(4-methoxybenzyloxy)ethyl)-5,6-dihydro-2H-pyran-2-yl)methyl)-1,3-dioxan-2-one
• CAS No.: 1262963-94-9
• Molecular Formula: C₂₁H₂₇IO₆
• Molecular Weight: 502.346
• Mol file: 1262963-94-9.mol

Synonyms:(4S,6S)-4-(iodomethyl)-6-(((2R,6S)-6-(2-(4-methoxybenzyloxy)ethyl)-5,6-dihydro-2H-pyran-2-yl)methyl)-1,3-dioxan-2-one

Chemical Property of (4S,6S)-4-(iodomethyl)-6-(((2R,6S)-6-(2-(4-methoxybenzyloxy)ethyl)-5,6-dihydro-2H-pyran-2-yl)methyl)-1,3-dioxan-2-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (4S,6S)-4-(iodomethyl)-6-(((2R,6S)-6-(2-(4-methoxybenzyloxy)ethyl)-5,6-dihydro-2H-pyran-2-yl)methyl)-1,3-dioxan-2-one

There total 8 articles about (4S,6S)-4-(iodomethyl)-6-(((2R,6S)-6-(2-(4-methoxybenzyloxy)ethyl)-5,6-dihydro-2H-pyran-2-yl)methyl)-1,3-dioxan-2-one 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: 92.0%

tert-butyl (R)-1-((2R,6S)-6-(2-(4-methoxybenzyloxy)ethyl)-5,6-dihydro-2H-pyran-2-yl)pent-4-en-2-yl carbonate (1262963-99-4) → (4S,6S)-4-(iodomethyl)-6-(((2R,6S)-6-(2-(4-methoxybenzyloxy)ethyl)-5,6-dihydro-2H-pyran-2-yl)methyl)-1,3-dioxan-2-one (1262963-94-9)

Guidance literature:

With N-iodo-succinimide; In acetonitrile; at -40 - 0 ℃;

DOI:10.1021/ol1029854

Reference yield:

(R)-2-(2-((4-methoxybenzyl)oxy)ethyl)oxirane (195257-62-6) → (4S,6S)-4-(iodomethyl)-6-(((2R,6S)-6-(2-(4-methoxybenzyloxy)ethyl)-5,6-dihydro-2H-pyran-2-yl)methyl)-1,3-dioxan-2-one (1262963-94-9)

Guidance literature:

Multi-step reaction with 7 steps

1.1: copper(l) iodide / tetrahydrofuran / 0.5 h / 25 °C

1.2: 0.5 h / -20 °C

2.1: tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride / dichloromethane / 20 °C / Inert atmosphere

3.1: iodine / tetrahydrofuran / 0 - 20 °C

4.1: 2,6-dimethylpyridine; sodium periodate; osmium(VIII) oxide / 1,4-dioxane; water / 2 h / 20 °C

5.1: titanium(IV) isopropylate; (R)-1,1'-Bi-2-naphthol; titanium tetrachloride; silver(l) oxide / dichloromethane / -15 - 0 °C / Inert atmosphere; Darkness; Molecular sieve

6.1: dmap; triethylamine / dichloromethane / 5 h / 20 °C

7.1: N-iodo-succinimide / acetonitrile / -40 - 0 °C

With tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; 2,6-dimethylpyridine; titanium(IV) isopropylate; dmap; sodium periodate; N-iodo-succinimide; copper(l) iodide; osmium(VIII) oxide; iodine; (R)-1,1'-Bi-2-naphthol; titanium tetrachloride; triethylamine; silver(l) oxide; In tetrahydrofuran; 1,4-dioxane; dichloromethane; water; acetonitrile; 7.1: Bartlett-Smith iodo-carbonate cyclization reaction;

DOI:10.1021/ol1029854

Reference yield:

4-(p-methoxybenzyloxy)-1,2-epoxybutane (142860-84-2) → (4S,6S)-4-(iodomethyl)-6-(((2R,6S)-6-(2-(4-methoxybenzyloxy)ethyl)-5,6-dihydro-2H-pyran-2-yl)methyl)-1,3-dioxan-2-one (1262963-94-9)

Guidance literature:

Multi-step reaction with 8 steps

1.1: (-)-chloro((1R,2R)-4,4',6,6'-tetra-tert-butyl-2,2'-[cyclohexane-1,2-diylbis(nitrilomethylidyne)]diphenolato)manganese(III); water / 0 - 20 °C

2.1: copper(l) iodide / tetrahydrofuran / 0.5 h / 25 °C

2.2: 0.5 h / -20 °C

3.1: tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride / dichloromethane / 20 °C / Inert atmosphere

4.1: iodine / tetrahydrofuran / 0 - 20 °C

5.1: 2,6-dimethylpyridine; sodium periodate; osmium(VIII) oxide / 1,4-dioxane; water / 2 h / 20 °C

6.1: titanium(IV) isopropylate; (R)-1,1'-Bi-2-naphthol; titanium tetrachloride; silver(l) oxide / dichloromethane / -15 - 0 °C / Inert atmosphere; Darkness; Molecular sieve

7.1: dmap; triethylamine / dichloromethane / 5 h / 20 °C

8.1: N-iodo-succinimide / acetonitrile / -40 - 0 °C

With tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; 2,6-dimethylpyridine; titanium(IV) isopropylate; dmap; sodium periodate; N-iodo-succinimide; copper(l) iodide; osmium(VIII) oxide; (-)-chloro((1R,2R)-4,4',6,6'-tetra-tert-butyl-2,2'-[cyclohexane-1,2-diylbis(nitrilomethylidyne)]diphenolato)manganese(III); water; iodine; (R)-1,1'-Bi-2-naphthol; titanium tetrachloride; triethylamine; silver(l) oxide; In tetrahydrofuran; 1,4-dioxane; dichloromethane; water; acetonitrile; 8.1: Bartlett-Smith iodo-carbonate cyclization reaction;

DOI:10.1021/ol1029854

upstream raw materials:

tert-butyl (R)-1-((2R,6S)-6-(2-(4-methoxybenzyloxy)ethyl)-5,6-dihydro-2H-pyran-2-yl)pent-4-en-2-yl carbonate

(S,E)-5-hydroxy-7-{(4-methoxybenzyl)oxy}hept-2-enal

(2S,6R)-6-allyl-2-[2-{(4-methoxybenzyl)oxy}ethyl]-3,6-dihydro-2H-pyran

2-[(2R,6S)-6-[2-{(4-methoxybenzyl)oxy}ethyl]-5,6-dihydro-2H-pyran-2-yl]acetaldehyde

Downstream raw materials:

(S)-1-((2R,6S)-6-(2-(4-methoxybenzyloxy)ethyl)-5,6-dihydro-2H-pyran-2-yl)-3-((S)-oxiran-2-yl)propan-2-ol

(2R,4R)-1-((2R,6S)-6-(2-(4-methoxybenzyloxy)ethyl)-5,6-dihydro-2H-pyran-2-yl)undecane-2,4-diol

(4R,6R)-4-heptyl-6-(((2R,6S)-6-(2-(4-methoxybenzyloxy)ethyl)-5,6-dihydro-2H-pyran-2-yl)methyl)-2,2-dimethyl-1,3-dioxane

C₂₁H₂₈O₆