(S)-4-((2R,4S,5R,6S)-5-Benzyloxy-6-dimethoxymethyl-4-methoxy-3,3-dimethyl-tetrahydro-pyran-2-ylmethyl)-[1,3]dioxolan-2-one

Base Information

• Chemical Name: (S)-4-((2R,4S,5R,6S)-5-Benzyloxy-6-dimethoxymethyl-4-methoxy-3,3-dimethyl-tetrahydro-pyran-2-ylmethyl)-[1,3]dioxolan-2-one
• CAS No.: 128271-04-5
• Molecular Formula: C₂₂H₃₂O₈
• Molecular Weight: 424.491
• Mol file: 128271-04-5.mol

Synonyms:(S)-4-((2R,4S,5R,6S)-5-Benzyloxy-6-dimethoxymethyl-4-methoxy-3,3-dimethyl-tetrahydro-pyran-2-ylmethyl)-[1,3]dioxolan-2-one

Chemical Property of (S)-4-((2R,4S,5R,6S)-5-Benzyloxy-6-dimethoxymethyl-4-methoxy-3,3-dimethyl-tetrahydro-pyran-2-ylmethyl)-[1,3]dioxolan-2-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (S)-4-((2R,4S,5R,6S)-5-Benzyloxy-6-dimethoxymethyl-4-methoxy-3,3-dimethyl-tetrahydro-pyran-2-ylmethyl)-[1,3]dioxolan-2-one

There total 14 articles about (S)-4-((2R,4S,5R,6S)-5-Benzyloxy-6-dimethoxymethyl-4-methoxy-3,3-dimethyl-tetrahydro-pyran-2-ylmethyl)-[1,3]dioxolan-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:

(2S,3R,4R,6R)-3-Benzyloxy-4-methoxy-5,5-dimethyl-6-((S)-2-oxo-[1,3]dioxolan-4-ylmethyl)-tetrahydro-pyran-2-carbaldehyde + trimethyl orthoformate (149-73-5) → (S)-4-((2R,4R,5R,6S)-5-Benzyloxy-6-dimethoxymethyl-4-methoxy-3,3-dimethyl-tetrahydro-pyran-2-ylmethyl)-[1,3]dioxolan-2-one (128271-04-5)

Guidance literature:

With toluene-4-sulfonic acid; In methanol; at 0 - 25 ℃; Yield given;

DOI:10.1021/ja00025a056

Reference yield:

benzyl bromide (100-39-0) → (S)-4-((2R,4R,5R,6S)-5-Benzyloxy-6-dimethoxymethyl-4-methoxy-3,3-dimethyl-tetrahydro-pyran-2-ylmethyl)-[1,3]dioxolan-2-one (128271-04-5)

Guidance literature:

Multi-step reaction with 4 steps

2: 1.) OsO₄, S,S-Corey ligand / 1.) CH₂Cl₂, -90 deg C, 2.) C₆H₆, reflux

3: Swern's reagent

4: p-TsOH / methanol / 0 - 25 °C

With osmium(VIII) oxide; S,S-Corey ligand; Swern's reagent; toluene-4-sulfonic acid; In methanol;

DOI:10.1021/ja00025a056

Reference yield:

(2S,4aR,6S,8aS)-6-Methoxy-7,7-dimethyl-2-phenyl-tetrahydro-pyrano[3,2-d][1,3]dioxin-8-one (138050-79-0) → (S)-4-((2R,4R,5R,6S)-5-Benzyloxy-6-dimethoxymethyl-4-methoxy-3,3-dimethyl-tetrahydro-pyran-2-ylmethyl)-[1,3]dioxolan-2-one (128271-04-5)

Guidance literature:

Multi-step reaction with 6 steps

1: NaBH(OAc)3, CeCl₃ / methanol / 0 °C

2: NaH / tetrahydrofuran / Ambient temperature

4: 1.) OsO₄, S,S-Corey ligand / 1.) CH₂Cl₂, -90 deg C, 2.) C₆H₆, reflux

5: Swern's reagent

6: p-TsOH / methanol / 0 - 25 °C

With osmium(VIII) oxide; cerium(III) chloride; S,S-Corey ligand; Swern's reagent; sodium tris(acetoxy)borohydride; sodium hydride; toluene-4-sulfonic acid; In tetrahydrofuran; methanol;

DOI:10.1021/ja00025a056

upstream raw materials:

trimethyl(propargyl)silane

(S)-4-((2R,4S,5R,6S)-5-Benzyloxy-4,6-dimethoxy-3,3-dimethyl-tetrahydro-pyran-2-ylmethyl)-[1,3]dioxolan-2-one

((2S,4S,5R,6S)-5-Benzyloxy-4,6-dimethoxy-3,3-dimethyl-tetrahydro-pyran-2-yl)-methanol

(2R,4S,5R,6S)-2-Allyl-5-benzyloxy-4,6-dimethoxy-3,3-dimethyl-tetrahydro-pyran

Downstream raw materials:

mycalamide A

(S)-2-(3,4-Dimethoxy-benzyloxy)-2-((2R,5R,6R)-2-methoxy-5,6-dimethyl-4-methylene-tetrahydro-pyran-2-yl)-N-[(4R,4aS,6R,8S,8aR)-8-methoxy-7,7-dimethyl-6-((S)-2-oxo-[1,3]dioxolan-4-ylmethyl)-hexahydro-pyrano[3,2-d][1,3]dioxin-4-yl]-acetamide

(S)-2-(3,4-Dimethoxy-benzyloxy)-2-((2R,5R,6R)-2-methoxy-5,6-dimethyl-4-methylene-tetrahydro-pyran-2-yl)-N-[(4S,4aS,6R,8S,8aR)-8-methoxy-7,7-dimethyl-6-((S)-2-oxo-[1,3]dioxolan-4-ylmethyl)-hexahydro-pyrano[3,2-d][1,3]dioxin-4-yl]-acetamide