(3R,5S,6S)-6-[(2R,4S,5R)-5-((3aR,4R,6S,6aS)-6-Benzyloxy-4-ethyl-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl)-4-methyl-tetrahydro-furan-2-yl]-3,5-dimethyl-6-triethylsilanyloxy-1-(2-trimethylsilanyl-ethoxymethoxy)-hexan-2-ol

Base Information

• Chemical Name: (3R,5S,6S)-6-[(2R,4S,5R)-5-((3aR,4R,6S,6aS)-6-Benzyloxy-4-ethyl-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl)-4-methyl-tetrahydro-furan-2-yl]-3,5-dimethyl-6-triethylsilanyloxy-1-(2-trimethylsilanyl-ethoxymethoxy)-hexan-2-ol
• CAS No.: 1053717-30-8
• Molecular Formula: C₄₁H₇₄O₉Si₂
• Molecular Weight: 767.204

Synonyms:(3R,5S,6S)-6-[(2R,4S,5R)-5-((3aR,4R,6S,6aS)-6-Benzyloxy-4-ethyl-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl)-4-methyl-tetrahydro-furan-2-yl]-3,5-dimethyl-6-triethylsilanyloxy-1-(2-trimethylsilanyl-ethoxymethoxy)-hexan-2-ol

Chemical Property of (3R,5S,6S)-6-[(2R,4S,5R)-5-((3aR,4R,6S,6aS)-6-Benzyloxy-4-ethyl-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl)-4-methyl-tetrahydro-furan-2-yl]-3,5-dimethyl-6-triethylsilanyloxy-1-(2-trimethylsilanyl-ethoxymethoxy)-hexan-2-ol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3R,5S,6S)-6-[(2R,4S,5R)-5-((3aR,4R,6S,6aS)-6-Benzyloxy-4-ethyl-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl)-4-methyl-tetrahydro-furan-2-yl]-3,5-dimethyl-6-triethylsilanyloxy-1-(2-trimethylsilanyl-ethoxymethoxy)-hexan-2-ol

There total 19 articles about (3R,5S,6S)-6-[(2R,4S,5R)-5-((3aR,4R,6S,6aS)-6-Benzyloxy-4-ethyl-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl)-4-methyl-tetrahydro-furan-2-yl]-3,5-dimethyl-6-triethylsilanyloxy-1-(2-trimethylsilanyl-ethoxymethoxy)-hexan-2-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:

benzyl 2,3-O-(1-methylethylidene)-α-D-lyxofuranosiduronic acid chloride (96150-86-6) → (3R,5S,6S)-6-[(2R,4S,5R)-5-((3aR,4R,6S,6aS)-6-Benzyloxy-4-ethyl-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl)-4-methyl-tetrahydro-furan-2-yl]-3,5-dimethyl-6-triethylsilanyloxy-1-(2-trimethylsilanyl-ethoxymethoxy)-hexan-2-ol (1053717-30-8)

Guidance literature:

Multi-step reaction with 18 steps

1: 1.) TMSCl, HMPA, 2.) LDA, 3.) LAH / 1.) -100 deg C, 2.) RT

2: 88 percent / Dess-Martin reagent

3: 70 percent

4: 94 percent / CsF / hexamethylphosphoric acid triamide / 15 h / 125 °C

5: 96 percent / H₂, BF₄ / CH₂Cl₂ / 2 h / 33097.5 Torr

6: Dess-Martin periodinane / CH₂Cl₂ / 4 h

7: 1.) t-BuOK, n-BuLi, 2.) (-)-B-methoxydiisopinocampheylborane, BF₃*OEt₂, 3.) 3 N aq. NaOH, 30percent aq. H₂O₂

8: 2,6-lutidine / CH₂Cl₂ / 1 h

9: 1.) aq. N-methylmorpholine N-oxide, (NMO), OsO₄, 2.) aq. NaIO₄ / 1.) THF, benzene, RT, 12 h, 2.) THF, benzene, 2 h

10: toluene / 1.) 70 deg C, 10 h, 2.) reflux, 12 h

11: 1.) 1.0 M DIBAL, 2.) aq. potassium sodium tartrate / 1.) CH₂Cl₂, hexane, -78 deg C, 30 min, 2.) CH₂Cl₂, hexane, 3 h

12: 98 percent / pyridine / CH₂Cl₂ / 2 h

13: 99 percent / 48 aq. HF / acetonitrile / 0.67 h

14: 99 percent / H₂, BF₄ / CH₂Cl₂ / 3.5 h / 51714.8 Torr

15: 99 percent / 2,6-lutidine / CH₂Cl₂ / 0.17 h

16: 1.) DIBAL, 2.) 0.5 M aq. potassium sodium tartrate / 1.) CH₂Cl₂, hexane, -78 deg C, 30 min, 2.) CH₂Cl₂, hexane, 0 deg C, 2 h

17: Dess-Martin periodinane, pyridine / CH₂Cl₂ / 1.5 h

18: 1.) n-BuLi / 1.) THF, hexane, -78 deg C, 5 min, 2.) THF, hexane, -78 deg C, 10 min

With pyridine; (-)-B-methoxydiisopinocamphenylborane; 2,6-dimethylpyridine; N,N,N,N,N,N-hexamethylphosphoric triamide; sodium hydroxide; sodium periodate; osmium(VIII) oxide; lithium aluminium tetrahydride; n-butyllithium; chloro-trimethyl-silane; [(bicyclo[2.2.1]hepta-2,5-diene)(1,4-bis(diphenylphosphino)butane)rhodium(I)] tetrafluoroborate; BF4; boron trifluoride diethyl etherate; hydrogen fluoride; potassium tert-butylate; hydrogen; dihydrogen peroxide; diisobutylaluminium hydride; Dess-Martin periodane; Rochelle's salt; 4-methylmorpholine N-oxide; cesium fluoride; lithium diisopropyl amide; In N,N,N,N,N,N-hexamethylphosphoric triamide; dichloromethane; toluene; acetonitrile;

DOI:10.1021/ja00069a013

Reference yield:

2(R)-ethyl-2-<5(R)-(formyl)-3(S)-methyl-2(R)-tetrahydrofuryl>-3(R),4(S)-<(dimethylmethylene)dioxy>-5(S)-(benzyloxy)tetrahydrofuran → (3R,5S,6S)-6-[(2R,4S,5R)-5-((3aR,4R,6S,6aS)-6-Benzyloxy-4-ethyl-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl)-4-methyl-tetrahydro-furan-2-yl]-3,5-dimethyl-6-triethylsilanyloxy-1-(2-trimethylsilanyl-ethoxymethoxy)-hexan-2-ol (1053717-30-8)

Guidance literature:

Multi-step reaction with 12 steps

1: 1.) t-BuOK, n-BuLi, 2.) (-)-B-methoxydiisopinocampheylborane, BF₃*OEt₂, 3.) 3 N aq. NaOH, 30percent aq. H₂O₂

2: 2,6-lutidine / CH₂Cl₂ / 1 h

3: 1.) aq. N-methylmorpholine N-oxide, (NMO), OsO₄, 2.) aq. NaIO₄ / 1.) THF, benzene, RT, 12 h, 2.) THF, benzene, 2 h

4: toluene / 1.) 70 deg C, 10 h, 2.) reflux, 12 h

5: 1.) 1.0 M DIBAL, 2.) aq. potassium sodium tartrate / 1.) CH₂Cl₂, hexane, -78 deg C, 30 min, 2.) CH₂Cl₂, hexane, 3 h

6: 98 percent / pyridine / CH₂Cl₂ / 2 h

7: 99 percent / 48 aq. HF / acetonitrile / 0.67 h

8: 99 percent / H₂, BF₄ / CH₂Cl₂ / 3.5 h / 51714.8 Torr

9: 99 percent / 2,6-lutidine / CH₂Cl₂ / 0.17 h

10: 1.) DIBAL, 2.) 0.5 M aq. potassium sodium tartrate / 1.) CH₂Cl₂, hexane, -78 deg C, 30 min, 2.) CH₂Cl₂, hexane, 0 deg C, 2 h

11: Dess-Martin periodinane, pyridine / CH₂Cl₂ / 1.5 h

12: 1.) n-BuLi / 1.) THF, hexane, -78 deg C, 5 min, 2.) THF, hexane, -78 deg C, 10 min

With pyridine; (-)-B-methoxydiisopinocamphenylborane; 2,6-dimethylpyridine; sodium hydroxide; sodium periodate; osmium(VIII) oxide; n-butyllithium; BF4; boron trifluoride diethyl etherate; hydrogen fluoride; potassium tert-butylate; hydrogen; dihydrogen peroxide; diisobutylaluminium hydride; Dess-Martin periodane; Rochelle's salt; 4-methylmorpholine N-oxide; In dichloromethane; toluene; acetonitrile;

DOI:10.1021/ja00069a013

Reference yield:

2(R)-ethyl-2-<5(R)-(hydroxymethyl)-3(S)-methyl-2(R)-tetrahydrofuryl>-3(R),4(S)-<(dimethylmethylene)dioxy>-5(S)-(benzyloxy)tetrahydrofuran (150019-30-0) → (3R,5S,6S)-6-[(2R,4S,5R)-5-((3aR,4R,6S,6aS)-6-Benzyloxy-4-ethyl-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl)-4-methyl-tetrahydro-furan-2-yl]-3,5-dimethyl-6-triethylsilanyloxy-1-(2-trimethylsilanyl-ethoxymethoxy)-hexan-2-ol (1053717-30-8)

Guidance literature:

Multi-step reaction with 13 steps

1: Dess-Martin periodinane / CH₂Cl₂ / 4 h

2: 1.) t-BuOK, n-BuLi, 2.) (-)-B-methoxydiisopinocampheylborane, BF₃*OEt₂, 3.) 3 N aq. NaOH, 30percent aq. H₂O₂

3: 2,6-lutidine / CH₂Cl₂ / 1 h

4: 1.) aq. N-methylmorpholine N-oxide, (NMO), OsO₄, 2.) aq. NaIO₄ / 1.) THF, benzene, RT, 12 h, 2.) THF, benzene, 2 h

5: toluene / 1.) 70 deg C, 10 h, 2.) reflux, 12 h

6: 1.) 1.0 M DIBAL, 2.) aq. potassium sodium tartrate / 1.) CH₂Cl₂, hexane, -78 deg C, 30 min, 2.) CH₂Cl₂, hexane, 3 h

7: 98 percent / pyridine / CH₂Cl₂ / 2 h

8: 99 percent / 48 aq. HF / acetonitrile / 0.67 h

9: 99 percent / H₂, BF₄ / CH₂Cl₂ / 3.5 h / 51714.8 Torr

10: 99 percent / 2,6-lutidine / CH₂Cl₂ / 0.17 h

11: 1.) DIBAL, 2.) 0.5 M aq. potassium sodium tartrate / 1.) CH₂Cl₂, hexane, -78 deg C, 30 min, 2.) CH₂Cl₂, hexane, 0 deg C, 2 h

12: Dess-Martin periodinane, pyridine / CH₂Cl₂ / 1.5 h

13: 1.) n-BuLi / 1.) THF, hexane, -78 deg C, 5 min, 2.) THF, hexane, -78 deg C, 10 min

With pyridine; (-)-B-methoxydiisopinocamphenylborane; 2,6-dimethylpyridine; sodium hydroxide; sodium periodate; osmium(VIII) oxide; n-butyllithium; BF4; boron trifluoride diethyl etherate; hydrogen fluoride; potassium tert-butylate; hydrogen; dihydrogen peroxide; diisobutylaluminium hydride; Dess-Martin periodane; Rochelle's salt; 4-methylmorpholine N-oxide; In dichloromethane; toluene; acetonitrile;

DOI:10.1021/ja00069a013

upstream raw materials:

benzyl 2,3-O-(1-methylethylidene)-α-D-lyxofuranosiduronic acid chloride

2(R)-ethyl-2-<5(R)-(hydroxymethyl)-3(S)-methyl-2(R)-tetrahydrofuryl>-3(R),4(S)-<(dimethylmethylene)dioxy>-5(S)-(benzyloxy)tetrahydrofuran

2(R)-ethyl-2-<5(R)-<2(S)-methyl-1(S)-<(triethylsilyl)oxy>-3-butenyl>-3(S)-methyl-2(R)-tetrahydrofuryl>-3(R),4(S)-<(dimethylmethylene)dioxy>-5(S)-(benzyloxy)tetrahydrofuran

2(R)-ethyl-2-<5(R)-<4-((benzyloxy)methyl)-1(S)-hydroxy-2(S)-methyl-3-pentenyl>-3(S)-methyl-2(R)-tetrahydrofuryl>-3(R),4(S)-<(dimethylmethylene)dioxy>-5(S)-(benzyloxy)tetrahydrofuran

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