5-((3S,4S,5R,6S)-4,5-Bis-benzyloxy-6-methoxy-2-methylene-tetrahydro-pyran-3-yloxymethyl)-6-iodo-benzo[1,3]dioxole

Base Information

• Chemical Name: 5-((3S,4S,5R,6S)-4,5-Bis-benzyloxy-6-methoxy-2-methylene-tetrahydro-pyran-3-yloxymethyl)-6-iodo-benzo[1,3]dioxole
• CAS No.: 194800-96-9
• Molecular Formula: C₂₉H₂₉IO₇
• Molecular Weight: 616.45

Synonyms:5-((3S,4S,5R,6S)-4,5-Bis-benzyloxy-6-methoxy-2-methylene-tetrahydro-pyran-3-yloxymethyl)-6-iodo-benzo[1,3]dioxole

Chemical Property of 5-((3S,4S,5R,6S)-4,5-Bis-benzyloxy-6-methoxy-2-methylene-tetrahydro-pyran-3-yloxymethyl)-6-iodo-benzo[1,3]dioxole

Chemical Property:

Purity/Quality:

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Technology Process of 5-((3S,4S,5R,6S)-4,5-Bis-benzyloxy-6-methoxy-2-methylene-tetrahydro-pyran-3-yloxymethyl)-6-iodo-benzo[1,3]dioxole

There total 3 articles about 5-((3S,4S,5R,6S)-4,5-Bis-benzyloxy-6-methoxy-2-methylene-tetrahydro-pyran-3-yloxymethyl)-6-iodo-benzo[1,3]dioxole 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%

methyl 6-deoxy-6-iodo-2,3-bis-O-(phenylmethyl)-α-D-glucopyranoside (87326-88-3) + 5-(chloromethyl)-6-iodobenzo[d][1,3]dioxole (65673-83-8) → 5-((3S,4S,5R,6S)-4,5-Bis-benzyloxy-6-methoxy-2-methylene-tetrahydro-pyran-3-yloxymethyl)-6-iodo-benzo[1,3]dioxole (194800-96-9)

Guidance literature:

With sodium hydride; In N,N-dimethyl-formamide; Ambient temperature;

DOI:10.1016/S0040-4039(97)01325-7

Reference yield:

6-iodo-1,3-benzodioxole-5-methanol (69048-76-6) → 5-((3S,4S,5R,6S)-4,5-Bis-benzyloxy-6-methoxy-2-methylene-tetrahydro-pyran-3-yloxymethyl)-6-iodo-benzo[1,3]dioxole (194800-96-9)

Guidance literature:

Multi-step reaction with 2 steps

1: 87 percent / MeSO₂Cl, Et₃N

2: 92 percent / NaH / dimethylformamide / Ambient temperature

With sodium hydride; methanesulfonyl chloride; triethylamine; In N,N-dimethyl-formamide;

DOI:10.1016/S0040-4039(97)01325-7

Reference yield:

piperonol (495-76-1) → 5-((3S,4S,5R,6S)-4,5-Bis-benzyloxy-6-methoxy-2-methylene-tetrahydro-pyran-3-yloxymethyl)-6-iodo-benzo[1,3]dioxole (194800-96-9)

Guidance literature:

Multi-step reaction with 3 steps

1: 78 percent / I₂, Ag(OOCCF₃)2

2: 87 percent / MeSO₂Cl, Et₃N

3: 92 percent / NaH / dimethylformamide / Ambient temperature

With Ag(OOCCF₃)2; iodine; sodium hydride; methanesulfonyl chloride; triethylamine; In N,N-dimethyl-formamide;

DOI:10.1016/S0040-4039(97)01325-7

upstream raw materials:

methyl 6-deoxy-6-iodo-2,3-bis-O-(phenylmethyl)-α-D-glucopyranoside

5-(chloromethyl)-6-iodobenzo[d][1,3]dioxole

6-iodo-1,3-benzodioxole-5-methanol

piperonol

Downstream raw materials:

(2S,3R,4S,5S)-3,4-Bis-benzyloxy-5-hydroxy-2-(6-iodo-benzo[1,3]dioxol-5-ylmethoxy)-cyclohexanone

(4R,5S,6R)-5,6-Bis-benzyloxy-4-(6-iodo-benzo[1,3]dioxol-5-ylmethoxy)-cyclohex-2-enone

Methanesulfonic acid (1R,2S,3R,4S,5S)-3,4-bis-benzyloxy-5-hydroxy-2-(6-iodo-benzo[1,3]dioxol-5-ylmethoxy)-cyclohexyl ester

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