(2S,3S,4R,4aR,6R,7S,8aR)-4-Benzyloxy-7-(tert-butyl-dimethyl-silanyloxy)-6-[2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-2-(2-iodo-ethyl)-octahydro-pyrano[3,2-b]pyran-3-ol

Base Information

• Chemical Name: (2S,3S,4R,4aR,6R,7S,8aR)-4-Benzyloxy-7-(tert-butyl-dimethyl-silanyloxy)-6-[2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-2-(2-iodo-ethyl)-octahydro-pyrano[3,2-b]pyran-3-ol
• CAS No.: 199792-35-3
• Molecular Formula: C₄₁H₅₉IO₆Si₂
• Molecular Weight: 830.991

Synonyms:(2S,3S,4R,4aR,6R,7S,8aR)-4-Benzyloxy-7-(tert-butyl-dimethyl-silanyloxy)-6-[2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-2-(2-iodo-ethyl)-octahydro-pyrano[3,2-b]pyran-3-ol

Chemical Property of (2S,3S,4R,4aR,6R,7S,8aR)-4-Benzyloxy-7-(tert-butyl-dimethyl-silanyloxy)-6-[2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-2-(2-iodo-ethyl)-octahydro-pyrano[3,2-b]pyran-3-ol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,3S,4R,4aR,6R,7S,8aR)-4-Benzyloxy-7-(tert-butyl-dimethyl-silanyloxy)-6-[2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-2-(2-iodo-ethyl)-octahydro-pyrano[3,2-b]pyran-3-ol

There total 37 articles about (2S,3S,4R,4aR,6R,7S,8aR)-4-Benzyloxy-7-(tert-butyl-dimethyl-silanyloxy)-6-[2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-2-(2-iodo-ethyl)-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: 86.0%

Toluene-4-sulfonic acid 2-{(2S,3S,4R,4aR,6R,7S,8aR)-4-benzyloxy-7-(tert-butyl-dimethyl-silanyloxy)-6-[2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-3-hydroxy-octahydro-pyrano[3,2-b]pyran-2-yl}-ethyl ester (199792-34-2) → (2S,3S,4R,4aR,6R,7S,8aR)-4-Benzyloxy-7-(tert-butyl-dimethyl-silanyloxy)-6-[2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-2-(2-iodo-ethyl)-octahydro-pyrano[3,2-b]pyran-3-ol (199792-35-3)

Guidance literature:

With sodium iodide; In acetone; at 50 ℃; for 8h;

DOI:10.1016/S0040-4039(97)10107-1 DOI:10.1016/S0040-4020(97)10254-X

Reference yield:

(Z)-5-{(2R,3R,4R,5S,6S)-4,5-Bis-benzyloxy-3-(4-methoxy-benzyloxy)-6-[2-(4-methoxy-benzyloxy)-ethyl]-tetrahydro-pyran-2-yl}-4-(tert-butyl-dimethyl-silanyloxy)-pent-2-enoic acid methyl ester → (2S,3S,4R,4aR,6R,7S,8aR)-4-Benzyloxy-7-(tert-butyl-dimethyl-silanyloxy)-6-[2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-2-(2-iodo-ethyl)-octahydro-pyrano[3,2-b]pyran-3-ol (199792-35-3)

Guidance literature:

Multi-step reaction with 12 steps

1: 22 percent / DDQ / CH₂Cl₂; H₂O / 0.5 h / Ambient temperature

2: 1) NaH, 2) t-BuOK / 1) THF, room temperature, 2 h, 2) MeOH, room temperature, 18 h

3: 75 percent / TfOH / diethyl ether / 0.17 h / Ambient temperature

4: 100 percent / LiAlH₄ / diethyl ether / 0.5 h / -5 °C

5: 95 percent / NEt₃, DMAP / CH₂Cl₂ / 9 h / Ambient temperature

6: 100 percent / DDQ / CH₂Cl₂; H₂O / 0.67 h / Ambient temperature

7: 44 percent / H₂ / Pd(OH)2-C / ethanol; ethyl acetate / 168 h / 760 Torr / Ambient temperature

8: 96 percent / p-TsOH*H₂O / 0.5 h / Ambient temperature

9: 99 percent / NaH, tetrabutylammonium iodide / tetrahydrofuran / 31 h / Ambient temperature

10: 94 percent / p-TsOH*H₂O / methanol / 0.83 h / Ambient temperature

11: 83 percent / NEt₃, DMAP / CH₂Cl₂ / 3 h / Ambient temperature

12: 86 percent / NaI / acetone / 8 h / 50 °C

With dmap; lithium aluminium tetrahydride; trifluorormethanesulfonic acid; potassium tert-butylate; hydrogen; tetra-(n-butyl)ammonium iodide; sodium hydride; toluene-4-sulfonic acid; triethylamine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; sodium iodide; palladium hydroxide - carbon; In tetrahydrofuran; methanol; diethyl ether; ethanol; dichloromethane; water; ethyl acetate; acetone;

DOI:10.1016/S0040-4020(97)10254-X

Reference yield:

{(2R,3R,4aR,6S,7S,8R,8aR)-7,8-Bis-benzyloxy-3-(tert-butyl-dimethyl-silanyloxy)-6-[2-(4-methoxy-benzyloxy)-ethyl]-octahydro-pyrano[3,2-b]pyran-2-yl}-acetic acid methyl ester (199792-29-5) → (2S,3S,4R,4aR,6R,7S,8aR)-4-Benzyloxy-7-(tert-butyl-dimethyl-silanyloxy)-6-[2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-2-(2-iodo-ethyl)-octahydro-pyrano[3,2-b]pyran-3-ol (199792-35-3)

Guidance literature:

Multi-step reaction with 13 steps

1: 99 percent / LiAlH₄ / diethyl ether / 0.33 h / -5 °C

2: 100 percent / tetrabutylammonium fluoride / tetrahydrofuran / 0.5 h / Ambient temperature

3: 100 percent / NEt₃, DMAP / CH₂Cl₂ / 15 h / Ambient temperature

4: 1) (COCl)2, DMSO, 2) NEt₃ / 1) CH₂Cl₂, -78 deg C, 30 min, 2) CH₂Cl₂, 0 deg C, 10 min

5: 99 percent / LiAlH₄ / diethyl ether / 0.25 h / -20 °C

6: 97 percent / 2,6-lutidine / CH₂Cl₂ / 1 h / Ambient temperature

7: 100 percent / DDQ / CH₂Cl₂; H₂O / 0.67 h / Ambient temperature

8: 44 percent / H₂ / Pd(OH)2-C / ethanol; ethyl acetate / 168 h / 760 Torr / Ambient temperature

9: 96 percent / p-TsOH*H₂O / 0.5 h / Ambient temperature

10: 99 percent / NaH, tetrabutylammonium iodide / tetrahydrofuran / 31 h / Ambient temperature

11: 94 percent / p-TsOH*H₂O / methanol / 0.83 h / Ambient temperature

12: 83 percent / NEt₃, DMAP / CH₂Cl₂ / 3 h / Ambient temperature

13: 86 percent / NaI / acetone / 8 h / 50 °C

With 2,6-dimethylpyridine; dmap; lithium aluminium tetrahydride; oxalyl dichloride; tetrabutyl ammonium fluoride; hydrogen; tetra-(n-butyl)ammonium iodide; sodium hydride; toluene-4-sulfonic acid; dimethyl sulfoxide; triethylamine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; sodium iodide; palladium hydroxide - carbon; In tetrahydrofuran; methanol; diethyl ether; ethanol; dichloromethane; water; ethyl acetate; acetone;

DOI:10.1016/S0040-4020(97)10254-X

upstream raw materials:

Toluene-4-sulfonic acid 2-{(2S,3S,4R,4aR,6R,7S,8aR)-4-benzyloxy-7-(tert-butyl-dimethyl-silanyloxy)-6-[2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-3-hydroxy-octahydro-pyrano[3,2-b]pyran-2-yl}-ethyl ester

t-butyldimethylsiyl triflate

benzyl bromide

{(2R,3R,4aR,6S,7S,8R,8aR)-7,8-Bis-benzyloxy-3-(tert-butyl-dimethyl-silanyloxy)-6-[2-(4-methoxy-benzyloxy)-ethyl]-octahydro-pyrano[3,2-b]pyran-2-yl}-acetic acid methyl ester

Downstream raw materials:

(2S,3S,4S,4aR,6R,7S,8aR)-4-Benzyloxy-7-(tert-butyl-dimethyl-silanyloxy)-6-[2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-2-(2-iodo-ethyl)-3-trimethylsilanyloxy-octahydro-pyrano[3,2-b]pyran

(2S,3S,4R,4aR,6R,7S,8aR)-4-Benzyloxy-7-(tert-butyl-dimethyl-silanyloxy)-6-[2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-2-{(Z)-3-[(2S,3R)-3-((S)-2,2-dimethyl-[1,3]dioxolan-4-ylmethyl)-oxiranyl]-allyl}-octahydro-pyrano[3,2-b]pyran-3-ol

C₅₀H₇₂O₉Si₂

C₅₃H₈₀O₉Si₃

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