(2S,3S,4R,4aR,5aR,8S,9R,10aS,11aR)-3,4-Bis-benzyloxy-8-(1-ethoxy-ethoxy)-2-(2-methyl-[1,3]dithian-2-ylmethyl)-9-prop-2-ynyl-2,3,4,4a,5a,8,9,10a,11,11a-decahydro-1,5,10-trioxa-cyclohepta[b]naphthalene

Base Information

• Chemical Name: (2S,3S,4R,4aR,5aR,8S,9R,10aS,11aR)-3,4-Bis-benzyloxy-8-(1-ethoxy-ethoxy)-2-(2-methyl-[1,3]dithian-2-ylmethyl)-9-prop-2-ynyl-2,3,4,4a,5a,8,9,10a,11,11a-decahydro-1,5,10-trioxa-cyclohepta[b]naphthalene
• CAS No.: 344315-37-3
• Molecular Formula: C₃₉H₅₀O₇S₂
• Molecular Weight: 694.954
• Mol file: 344315-37-3.mol

Synonyms:

Chemical Property of (2S,3S,4R,4aR,5aR,8S,9R,10aS,11aR)-3,4-Bis-benzyloxy-8-(1-ethoxy-ethoxy)-2-(2-methyl-[1,3]dithian-2-ylmethyl)-9-prop-2-ynyl-2,3,4,4a,5a,8,9,10a,11,11a-decahydro-1,5,10-trioxa-cyclohepta[b]naphthalene

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,3S,4R,4aR,5aR,8S,9R,10aS,11aR)-3,4-Bis-benzyloxy-8-(1-ethoxy-ethoxy)-2-(2-methyl-[1,3]dithian-2-ylmethyl)-9-prop-2-ynyl-2,3,4,4a,5a,8,9,10a,11,11a-decahydro-1,5,10-trioxa-cyclohepta[b]naphthalene

There total 12 articles about (2S,3S,4R,4aR,5aR,8S,9R,10aS,11aR)-3,4-Bis-benzyloxy-8-(1-ethoxy-ethoxy)-2-(2-methyl-[1,3]dithian-2-ylmethyl)-9-prop-2-ynyl-2,3,4,4a,5a,8,9,10a,11,11a-decahydro-1,5,10-trioxa-cyclohepta[b]naphthalene 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:

(2S,3S,4R,4aR,6R,7S,8aR)-2-Allyl-3,4-bis-benzyloxy-6-(3,3-dibromo-allyl)-7-(1-ethoxy-ethoxy)-octahydro-pyrano[3,2-b]pyran → (2S,3S,4R,4aR,5aR,8S,9R,10aS,11aR)-3,4-Bis-benzyloxy-8-(1-ethoxy-ethoxy)-2-(2-methyl-[1,3]dithian-2-ylmethyl)-9-prop-2-ynyl-2,3,4,4a,5a,8,9,10a,11,11a-decahydro-1,5,10-trioxa-cyclohepta[b]naphthalene (344315-37-3)

Guidance literature:

Multi-step reaction with 12 steps

1.1: n-BuLi / tetrahydrofuran

2.1: Amberlyst-15E / methanol

3.1: Co₂(CO)8; BF₃*OEt₂ / CH₂Cl₂

3.2: propargyl alcohol / 1,2-dichloro-ethane / 60 °C

4.1: Jones' reagent / acetone

4.2: 88 percent / PdCl₂; CuCl / dimethylformamide; H₂O

5.1: 86 percent / I(collidine)2PF₆- / CH₂Cl₂

6.1: 90 percent / BF₃*OEt₂ / CH₂Cl₂

7.1: DIBAL-H / CH₂Cl₂

8.1: DBU / tetrahydrofuran

9.1: 81 percent / K₂CO₃ / methanol

10.1: 90 percent / BF₃*OEt₂ / CH₂Cl₂

11.1: p-nitro benzoic acid; DEAD; PPh₃ / toluene

11.2: 94 percent / K₂CO₃ / methanol

12.1: PPTS / CH₂Cl₂

With n-butyllithium; jones' reagent; dicobalt octacarbonyl; Amberlyst-15E; boron trifluoride diethyl etherate; pyridinium p-toluenesulfonate; diisobutylaluminium hydride; potassium carbonate; 1,8-diazabicyclo[5.4.0]undec-7-ene; triphenylphosphine; bis(2,4,6-trimethylpyridine)iodine(I) hexafluorophosphate; diethylazodicarboxylate; 4-nitro-benzoic acid; In tetrahydrofuran; methanol; dichloromethane; acetone; toluene; 4.1: Wacker oxidation / 11.1: modified Mitsunobu inversion;

DOI:10.1016/S0040-4039(01)00286-6

Reference yield:

(2S,3S,4R,4aR,5aR,8R,9R,10aS,11aR)-3,4-Bis-benzyloxy-2-(2-methyl-[1,3]dithian-2-ylmethyl)-9-prop-2-ynyl-2,3,4,4a,5a,8,9,10a,11,11a-decahydro-1,5,10-trioxa-cyclohepta[b]naphthalen-8-ol (344315-36-2) → (2S,3S,4R,4aR,5aR,8S,9R,10aS,11aR)-3,4-Bis-benzyloxy-8-(1-ethoxy-ethoxy)-2-(2-methyl-[1,3]dithian-2-ylmethyl)-9-prop-2-ynyl-2,3,4,4a,5a,8,9,10a,11,11a-decahydro-1,5,10-trioxa-cyclohepta[b]naphthalene (344315-37-3)

Guidance literature:

Multi-step reaction with 2 steps

1.1: p-nitro benzoic acid; DEAD; PPh₃ / toluene

1.2: 94 percent / K₂CO₃ / methanol

2.1: PPTS / CH₂Cl₂

With pyridinium p-toluenesulfonate; triphenylphosphine; diethylazodicarboxylate; 4-nitro-benzoic acid; In dichloromethane; toluene; 1.1: modified Mitsunobu inversion;

DOI:10.1016/S0040-4039(01)00286-6

Reference yield:

2-((2S,3S,4R,4aR,5aR,9R,10aS,11aR)-2-Allyl-3,4-bis-benzyloxy-7-triethylsilanyl-2,3,4,4a,5a,6,9,10a,11,11a-decahydro-1,5,10-trioxa-cyclohepta[b]naphthalen-9-yl)-ethanol (344315-31-7) → (2S,3S,4R,4aR,5aR,8S,9R,10aS,11aR)-3,4-Bis-benzyloxy-8-(1-ethoxy-ethoxy)-2-(2-methyl-[1,3]dithian-2-ylmethyl)-9-prop-2-ynyl-2,3,4,4a,5a,8,9,10a,11,11a-decahydro-1,5,10-trioxa-cyclohepta[b]naphthalene (344315-37-3)

Guidance literature:

Multi-step reaction with 9 steps

1.1: Jones' reagent / acetone

1.2: 88 percent / PdCl₂; CuCl / dimethylformamide; H₂O

2.1: 86 percent / I(collidine)2PF₆- / CH₂Cl₂

3.1: 90 percent / BF₃*OEt₂ / CH₂Cl₂

4.1: DIBAL-H / CH₂Cl₂

5.1: DBU / tetrahydrofuran

6.1: 81 percent / K₂CO₃ / methanol

7.1: 90 percent / BF₃*OEt₂ / CH₂Cl₂

8.1: p-nitro benzoic acid; DEAD; PPh₃ / toluene

8.2: 94 percent / K₂CO₃ / methanol

9.1: PPTS / CH₂Cl₂

With jones' reagent; boron trifluoride diethyl etherate; pyridinium p-toluenesulfonate; diisobutylaluminium hydride; potassium carbonate; 1,8-diazabicyclo[5.4.0]undec-7-ene; triphenylphosphine; bis(2,4,6-trimethylpyridine)iodine(I) hexafluorophosphate; diethylazodicarboxylate; 4-nitro-benzoic acid; In tetrahydrofuran; methanol; dichloromethane; acetone; toluene; 1.1: Wacker oxidation / 8.1: modified Mitsunobu inversion;

DOI:10.1016/S0040-4039(01)00286-6

upstream raw materials:

ethyl vinyl ether

(2S,3S,4R,4aR,5aR,8S,9R,10aS,11aR)-3,4-Bis-benzyloxy-2-(2-methyl-[1,3]dithian-2-ylmethyl)-9-prop-2-ynyl-2,3,4,4a,5a,8,9,10a,11,11a-decahydro-1,5,10-trioxa-cyclohepta[b]naphthalen-8-ol

(2S,3S,4R,4aR,5aR,8R,9R,10aS,11aR)-3,4-Bis-benzyloxy-2-(2-methyl-[1,3]dithian-2-ylmethyl)-9-prop-2-ynyl-2,3,4,4a,5a,8,9,10a,11,11a-decahydro-1,5,10-trioxa-cyclohepta[b]naphthalen-8-ol

2-((2S,3S,4R,4aR,5aR,9R,10aS,11aR)-2-Allyl-3,4-bis-benzyloxy-7-triethylsilanyl-2,3,4,4a,5a,6,9,10a,11,11a-decahydro-1,5,10-trioxa-cyclohepta[b]naphthalen-9-yl)-ethanol

Downstream raw materials:

C₄₁H₄₈O₇S₂

C₄₁H₅₆O₈Si

C₄₄H₆₀O₈S₂Si

C₅₀H₆₈O₇S₂Si