(R)-1-((2R,3R,4R,5R,6R)-3-Benzyloxy-5-hydroxy-6-hydroxymethyl-4-methoxymethoxy-tetrahydro-pyran-2-yl)-7-(tert-butyl-diphenyl-silanyloxy)-6-hydroxy-heptan-3-one

Base Information

• Chemical Name: (R)-1-((2R,3R,4R,5R,6R)-3-Benzyloxy-5-hydroxy-6-hydroxymethyl-4-methoxymethoxy-tetrahydro-pyran-2-yl)-7-(tert-butyl-diphenyl-silanyloxy)-6-hydroxy-heptan-3-one
• CAS No.: 115369-32-9
• Molecular Formula: C₃₈H₅₂O₉Si
• Molecular Weight: 680.911
• Mol file: 115369-32-9.mol

Synonyms:(R)-1-((2R,3R,4R,5R,6R)-3-Benzyloxy-5-hydroxy-6-hydroxymethyl-4-methoxymethoxy-tetrahydro-pyran-2-yl)-7-(tert-butyl-diphenyl-silanyloxy)-6-hydroxy-heptan-3-one

Chemical Property of (R)-1-((2R,3R,4R,5R,6R)-3-Benzyloxy-5-hydroxy-6-hydroxymethyl-4-methoxymethoxy-tetrahydro-pyran-2-yl)-7-(tert-butyl-diphenyl-silanyloxy)-6-hydroxy-heptan-3-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (R)-1-((2R,3R,4R,5R,6R)-3-Benzyloxy-5-hydroxy-6-hydroxymethyl-4-methoxymethoxy-tetrahydro-pyran-2-yl)-7-(tert-butyl-diphenyl-silanyloxy)-6-hydroxy-heptan-3-one

There total 21 articles about (R)-1-((2R,3R,4R,5R,6R)-3-Benzyloxy-5-hydroxy-6-hydroxymethyl-4-methoxymethoxy-tetrahydro-pyran-2-yl)-7-(tert-butyl-diphenyl-silanyloxy)-6-hydroxy-heptan-3-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:

(2R,3S,6R)-2-acetoxymethyl-6-allyl-3,6-dihydro-2H-pyran-3-yl acetate (82740-87-2) → (R)-1-((2R,3R,4R,5R,6R)-3-Benzyloxy-5-hydroxy-6-hydroxymethyl-4-methoxymethoxy-tetrahydro-pyran-2-yl)-7-(tert-butyl-diphenyl-silanyloxy)-6-hydroxy-heptan-3-one (115369-32-9)

Guidance literature:

Multi-step reaction with 17 steps

1: 89 percent / water, trimethylamine / methanol / Ambient temperature

2: 80 percent / d,l-camphorsulfonic acid / CH₂Cl₂ / Ambient temperature

3: 1.) diborane, 2.) 2N NaOH, 30percent H₂O₂ / 1.) THF, -25 deg C, 12 h, 2.) EtOH, RT, overnight

4: pyridine / Ambient temperature

5: MeOH, Dowex 50W (H+) / 9.5 h / Ambient temperature

6: MCPBA / CHCl₃ / 5 °C

7: d,l-camphorsulfonic acid / CHCl₃

8: sodium methoxide / methanol; tetrahydrofuran / 5 °C

9: 1.) DMSO, (COCl)2, 2.) triethylamine / 1.) CH₂Cl₂, -78 deg C, 2.) CH₂Cl₂, -78 deg C, 10 min.

10: PPTS / CH₂Cl₂ / Ambient temperature

11: 1.) sodium hydride / 1.) DMF, 5 deg C, overnight, 2.) DMF, 70 deg C, 3.5 h

12: 1.) potassium hydride / 1.) DMF, RT, 10 min; 2.) DMF, RT, 30 min.

13: 98 percent / 0.5N HCl / tetrahydrofuran / 3 h / Ambient temperature

14: 1.) n-BuLi / 1.) THF, -78 deg C, 30 min; 2.) THF, -78 deg C, 30 min.

15: 1.) DMSO, oxalyl chloride, 2.) triethylamine / 1.) CH₂Cl₂, -78 deg C, 15 min; 2.) CH₂Cl₂, -78 to 0 deg C

16: 1.) aluminium foil, 2percent HgCl₂ / 1.) MeOH, ether, 30 sec; 2.) THF, H₂O, 60 deg C, overnight

17: EtOH, acetic acid / 72 h / Heating

With pyridine; hydrogenchloride; methanol; sodium hydroxide; n-butyllithium; oxalyl dichloride; ethanol; Dowex 50W (H+); camphor-10-sulfonic acid; water; dihydrogen peroxide; sodium methylate; pyridinium p-toluenesulfonate; potassium hydride; sodium hydride; acetic acid; dimethyl sulfoxide; triethylamine; 3-chloro-benzenecarboperoxoic acid; aluminium; mercury dichloride; diborane; trimethylamine; In tetrahydrofuran; methanol; dichloromethane; chloroform;

DOI:10.1016/S0040-4020(01)86916-7

Reference yield:

(2R,3S,6R)-6-allyl-2-hydroxymethyl-3,6-dihydro-2H-pyran-3-ol (95791-07-4) → (R)-1-((2R,3R,4R,5R,6R)-3-Benzyloxy-5-hydroxy-6-hydroxymethyl-4-methoxymethoxy-tetrahydro-pyran-2-yl)-7-(tert-butyl-diphenyl-silanyloxy)-6-hydroxy-heptan-3-one (115369-32-9)

Guidance literature:

Multi-step reaction with 16 steps

1: 80 percent / d,l-camphorsulfonic acid / CH₂Cl₂ / Ambient temperature

2: 1.) diborane, 2.) 2N NaOH, 30percent H₂O₂ / 1.) THF, -25 deg C, 12 h, 2.) EtOH, RT, overnight

3: pyridine / Ambient temperature

4: MeOH, Dowex 50W (H+) / 9.5 h / Ambient temperature

5: MCPBA / CHCl₃ / 5 °C

6: d,l-camphorsulfonic acid / CHCl₃

7: sodium methoxide / methanol; tetrahydrofuran / 5 °C

8: 1.) DMSO, (COCl)2, 2.) triethylamine / 1.) CH₂Cl₂, -78 deg C, 2.) CH₂Cl₂, -78 deg C, 10 min.

9: PPTS / CH₂Cl₂ / Ambient temperature

10: 1.) sodium hydride / 1.) DMF, 5 deg C, overnight, 2.) DMF, 70 deg C, 3.5 h

11: 1.) potassium hydride / 1.) DMF, RT, 10 min; 2.) DMF, RT, 30 min.

12: 98 percent / 0.5N HCl / tetrahydrofuran / 3 h / Ambient temperature

13: 1.) n-BuLi / 1.) THF, -78 deg C, 30 min; 2.) THF, -78 deg C, 30 min.

14: 1.) DMSO, oxalyl chloride, 2.) triethylamine / 1.) CH₂Cl₂, -78 deg C, 15 min; 2.) CH₂Cl₂, -78 to 0 deg C

15: 1.) aluminium foil, 2percent HgCl₂ / 1.) MeOH, ether, 30 sec; 2.) THF, H₂O, 60 deg C, overnight

16: EtOH, acetic acid / 72 h / Heating

With pyridine; hydrogenchloride; methanol; sodium hydroxide; n-butyllithium; oxalyl dichloride; ethanol; Dowex 50W (H+); camphor-10-sulfonic acid; dihydrogen peroxide; sodium methylate; pyridinium p-toluenesulfonate; potassium hydride; sodium hydride; acetic acid; dimethyl sulfoxide; triethylamine; 3-chloro-benzenecarboperoxoic acid; aluminium; mercury dichloride; diborane; In tetrahydrofuran; methanol; dichloromethane; chloroform;

DOI:10.1016/S0040-4020(01)86916-7

Reference yield:

Benzoic acid 3-((1S,2R,4R,5R,6R)-5-hydroxy-4-hydroxymethyl-3,7-dioxa-bicyclo[4.1.0]hept-2-yl)-propyl ester → (R)-1-((2R,3R,4R,5R,6R)-3-Benzyloxy-5-hydroxy-6-hydroxymethyl-4-methoxymethoxy-tetrahydro-pyran-2-yl)-7-(tert-butyl-diphenyl-silanyloxy)-6-hydroxy-heptan-3-one (115369-32-9)

Guidance literature:

Multi-step reaction with 11 steps

1: d,l-camphorsulfonic acid / CHCl₃

2: sodium methoxide / methanol; tetrahydrofuran / 5 °C

3: 1.) DMSO, (COCl)2, 2.) triethylamine / 1.) CH₂Cl₂, -78 deg C, 2.) CH₂Cl₂, -78 deg C, 10 min.

4: PPTS / CH₂Cl₂ / Ambient temperature

5: 1.) sodium hydride / 1.) DMF, 5 deg C, overnight, 2.) DMF, 70 deg C, 3.5 h

6: 1.) potassium hydride / 1.) DMF, RT, 10 min; 2.) DMF, RT, 30 min.

7: 98 percent / 0.5N HCl / tetrahydrofuran / 3 h / Ambient temperature

8: 1.) n-BuLi / 1.) THF, -78 deg C, 30 min; 2.) THF, -78 deg C, 30 min.

9: 1.) DMSO, oxalyl chloride, 2.) triethylamine / 1.) CH₂Cl₂, -78 deg C, 15 min; 2.) CH₂Cl₂, -78 to 0 deg C

10: 1.) aluminium foil, 2percent HgCl₂ / 1.) MeOH, ether, 30 sec; 2.) THF, H₂O, 60 deg C, overnight

11: EtOH, acetic acid / 72 h / Heating

With hydrogenchloride; n-butyllithium; oxalyl dichloride; ethanol; camphor-10-sulfonic acid; sodium methylate; pyridinium p-toluenesulfonate; potassium hydride; sodium hydride; acetic acid; dimethyl sulfoxide; triethylamine; aluminium; mercury dichloride; In tetrahydrofuran; methanol; dichloromethane; chloroform;

DOI:10.1016/S0040-4020(01)86916-7

upstream raw materials:

(R)-1-((4aR,6R,7R,8S,8aR)-7-Benzyloxy-8-methoxymethoxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-6-yl)-7-(tert-butyl-diphenyl-silanyloxy)-6-(1-ethoxy-ethoxy)-heptan-3-one

(2R,3S,6R)-2-acetoxymethyl-6-allyl-3,6-dihydro-2H-pyran-3-yl acetate

(2R,3S,6R)-6-allyl-2-hydroxymethyl-3,6-dihydro-2H-pyran-3-ol

3-((1aS,2R,3aR,7aR,7bS)-6-Phenyl-hexahydro-1,3,5,7-tetraoxa-cyclopropa[a]naphthalen-2-yl)-propionaldehyde

Downstream raw materials:

C₃₁H₄₄O₈Si

C₃₈H₅₀O₈Si

C₃₈H₄₈O₈Si

C₅₇H₆₄O₈Si

Refernces

• 1、 Isobe, Minoru,Ichikawa, Yoshiyasu,Goto, Toshio. "SYNTHETIC STUDIES TOWARD MARINE TOXIC POLYETHERS THE TOTAL SYNTHESIS OF OKADAIC ACID". . p. 963 - 966. Retrieved 2007/10/02.