(2R,3R,4R,4aR,6R,8aR)-4-Benzyloxy-2-hydroxymethyl-6-methoxy-6-[3-(4-methoxy-benzyloxy)-propyl]-octahydro-pyrano[3,2-b]pyran-3-ol

Base Information

• Chemical Name: (2R,3R,4R,4aR,6R,8aR)-4-Benzyloxy-2-hydroxymethyl-6-methoxy-6-[3-(4-methoxy-benzyloxy)-propyl]-octahydro-pyrano[3,2-b]pyran-3-ol
• CAS No.: 203925-48-8
• Molecular Formula: C₂₈H₃₈O₈
• Molecular Weight: 502.605
• Mol file: 203925-48-8.mol

Synonyms:(2R,3R,4R,4aR,6R,8aR)-4-Benzyloxy-2-hydroxymethyl-6-methoxy-6-[3-(4-methoxy-benzyloxy)-propyl]-octahydro-pyrano[3,2-b]pyran-3-ol

Chemical Property of (2R,3R,4R,4aR,6R,8aR)-4-Benzyloxy-2-hydroxymethyl-6-methoxy-6-[3-(4-methoxy-benzyloxy)-propyl]-octahydro-pyrano[3,2-b]pyran-3-ol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2R,3R,4R,4aR,6R,8aR)-4-Benzyloxy-2-hydroxymethyl-6-methoxy-6-[3-(4-methoxy-benzyloxy)-propyl]-octahydro-pyrano[3,2-b]pyran-3-ol

There total 2 articles about (2R,3R,4R,4aR,6R,8aR)-4-Benzyloxy-2-hydroxymethyl-6-methoxy-6-[3-(4-methoxy-benzyloxy)-propyl]-octahydro-pyrano[3,2-b]pyran-3-ol 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:

methanol (67-56-1) + 1-[(2R,4aR,6R,7R,8S,8aR)-8-Benzyloxy-7-hydroxy-2-(4-methoxy-phenyl)-hexahydro-pyrano[3,2-d][1,3]dioxin-6-yl]-6-(4-methoxy-benzyloxy)-hexan-3-one (203925-47-7) → (2R,3R,4R,4aR,6R,8aR)-4-Benzyloxy-2-hydroxymethyl-6-methoxy-6-[3-(4-methoxy-benzyloxy)-propyl]-octahydro-pyrano[3,2-b]pyran-3-ol (203925-48-8)

Guidance literature:

With toluene-4-sulfonic acid; In benzene; for 3.5h; Heating;

DOI:10.1021/ja973287h

Reference yield:

methanol (67-56-1) + C11H15LiO2 + 3-[(2R,4aR,6R,7R,8R,8aR)-8-Benzyloxy-7-(tert-butyl-dimethyl-silanyloxy)-2-(4-methoxy-phenyl)-hexahydro-pyrano[3,2-d][1,3]dioxin-6-yl]-propionaldehyde (194039-11-7) → (2R,3R,4R,4aR,6R,8aR)-4-Benzyloxy-2-hydroxymethyl-6-methoxy-6-[3-(4-methoxy-benzyloxy)-propyl]-octahydro-pyrano[3,2-b]pyran-3-ol (203925-48-8)

Guidance literature:

Multistep reaction;

DOI:10.1021/ja9715206

Reference yield:

(2R,3R,4R,4aR,6R,8aR)-4-Benzyloxy-2-hydroxymethyl-6-methoxy-6-[3-(4-methoxy-benzyloxy)-propyl]-octahydro-pyrano[3,2-b]pyran-3-ol (203925-48-8) → okadaic acid (78111-17-8)

Guidance literature:

Multi-step reaction with 13 steps

1: Et₃N

2: 1.) Dess-Martin periodinane

3: TBAF / tetrahydrofuran

4: Dess-Martin periodinane

5: CeCl₃ / tetrahydrofuran / -78 °C

6: NaH/TBAI

7: DDQ / pH=7

8: Dess-Martin periodinane

9: 1.), 2.) Dess-Martin periodinane

10: 86 percent / i-Pr₂NEt/LiCl / acetonitrile

11: 1.) Corey's (S)-CBS/BH₃ system, 2.) TsOH / 1.), 2.) benzene

12: LiOH, H₂O / tetrahydrofuran

13: LiDBB / tetrahydrofuran

With lithium hydroxide; cerium(III) chloride; lithium 4,4′-di(tert-butyl)biphenyl; BH₃ system; tetrabutyl ammonium fluoride; water; tetra-(n-butyl)ammonium iodide; sodium hydride; Dess-Martin periodane; toluene-4-sulfonic acid; triethylamine; N-ethyl-N,N-diisopropylamine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; lithium chloride; (S)-1-methyl-3,3-diphenyl-hexahydropyrrolo[1,2-c][1,3,2]oxazaborole; In tetrahydrofuran; acetonitrile;

DOI:10.1021/ja9715206

upstream raw materials:

methanol

3-[(2R,4aR,6R,7R,8R,8aR)-8-Benzyloxy-7-(tert-butyl-dimethyl-silanyloxy)-2-(4-methoxy-phenyl)-hexahydro-pyrano[3,2-d][1,3]dioxin-6-yl]-propionaldehyde

1-[(2R,4aR,6R,7R,8S,8aR)-8-Benzyloxy-7-hydroxy-2-(4-methoxy-phenyl)-hexahydro-pyrano[3,2-d][1,3]dioxin-6-yl]-6-(4-methoxy-benzyloxy)-hexan-3-one

Downstream raw materials:

(2R,3R,4R,4aR,6R,8aR)-4-Benzyloxy-2-(tert-butyl-dimethyl-silanyloxymethyl)-6-methoxy-6-[3-(4-methoxy-benzyloxy)-propyl]-octahydro-pyrano[3,2-b]pyran-3-ol

(2S,4R,4aR,6R,8aR)-4-Benzyloxy-6-methoxy-6-[3-(4-methoxy-benzyloxy)-propyl]-3-methylene-octahydro-pyrano[3,2-b]pyran-2-carbaldehyde

{(2S,4R,4aR,6R,8aR)-4-Benzyloxy-6-methoxy-6-[3-(4-methoxy-benzyloxy)-propyl]-3-methylene-octahydro-pyrano[3,2-b]pyran-2-yl}-methanol

{(2S,4R,4aR,6R,8aR)-4-Benzyloxy-6-methoxy-6-[3-(4-methoxy-benzyloxy)-propyl]-3-methylene-octahydro-pyrano[3,2-b]pyran-2-ylmethoxy}-tert-butyl-dimethyl-silane