(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

Base Information

• Chemical Name: (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
• CAS No.: 194039-13-9
• Molecular Formula: C₃₄H₅₂O₈Si
• Molecular Weight: 616.868
• Mol file: 194039-13-9.mol

Synonyms:(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

Chemical Property of (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

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

There total 1 articles about (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 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:

tert-butyldimethylsilyl chloride (18162-48-6) + (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) → (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 (194039-13-9)

Guidance literature:

With triethylamine; Yield given;

DOI:10.1021/ja9715206

Reference yield:

(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 (194039-13-9) → okadaic acid (78111-17-8)

Guidance literature:

Multi-step reaction with 12 steps

1: 1.) Dess-Martin periodinane

2: TBAF / tetrahydrofuran

3: Dess-Martin periodinane

4: CeCl₃ / tetrahydrofuran / -78 °C

5: NaH/TBAI

6: DDQ / pH=7

7: Dess-Martin periodinane

8: 1.), 2.) Dess-Martin periodinane

9: 86 percent / i-Pr₂NEt/LiCl / acetonitrile

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

11: LiOH, H₂O / tetrahydrofuran

12: 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; 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

Reference yield:

(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 (194039-13-9) → 3-{(2S,4aR,6S,8R,8aR)-8-Benzyloxy-6-[(1S,3S)-1-benzyloxy-3-((2S,3R,6S)-3-methyl-1,7-dioxa-spiro[5.5]undec-2-yl)-butyl]-2-methoxy-7-methylene-octahydro-pyrano[3,2-b]pyran-2-yl}-propionaldehyde (203925-62-6)

Guidance literature:

Multi-step reaction with 8 steps

1: Dess-Martin periodinane, NaHCO₃ / CH₂Cl₂ / 2 h / Ambient temperature

2: toluene / 0.5 h / 90 °C

3: 83 percent / TBAF

4: 100 percent / Dess-Martin periodinane

5: 1.) t-BuLi, 2.) CeCl₃

6: 95 percent / NaH

7: 75 percent / DDQ, aq. phosphate buffer / CH₂Cl₂; 2-methyl-propan-2-ol / 0.25 h / Ambient temperature

8: 94 percent / Dess-Martin periodinane, NaHCO₃ / CH₂Cl₂ / 0.75 h / Ambient temperature

With phosphate buffer; cerium(III) chloride; tetrabutyl ammonium fluoride; tert.-butyl lithium; sodium hydride; sodium hydrogencarbonate; Dess-Martin periodane; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In dichloromethane; toluene; tert-butyl alcohol;

DOI:10.1021/ja973287h

upstream raw materials:

tert-butyldimethylsilyl chloride

(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

Downstream raw materials:

{(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

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

(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