(4aR,6R,7R,8S,8aR)-7-Benzyloxy-6-(3,3-dimethoxy-propyl)-8-methoxymethoxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxine

Base Information

Chemical Name:(4aR,6R,7R,8S,8aR)-7-Benzyloxy-6-(3,3-dimethoxy-propyl)-8-methoxymethoxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxine
CAS No.:95791-13-2
Molecular Formula:C₂₇H₃₆O₈
Molecular Weight:488.578
Hs Code.:

Synonyms:(4aR,6R,7R,8S,8aR)-7-Benzyloxy-6-(3,3-dimethoxy-propyl)-8-methoxymethoxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxine

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Chemical Property of (4aR,6R,7R,8S,8aR)-7-Benzyloxy-6-(3,3-dimethoxy-propyl)-8-methoxymethoxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxine

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Technology Process of (4aR,6R,7R,8S,8aR)-7-Benzyloxy-6-(3,3-dimethoxy-propyl)-8-methoxymethoxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxine

There total 14 articles about (4aR,6R,7R,8S,8aR)-7-Benzyloxy-6-(3,3-dimethoxy-propyl)-8-methoxymethoxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxine 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:

: 95791-07-4
(2R,3S,6R)-6-allyl-2-hydroxymethyl-3,6-dihydro-2H-pyran-3-ol

: 95791-13-2
(4aR,6R,7R,8S,8aR)-7-Benzyloxy-6-(3,3-dimethoxy-propyl)-8-methoxymethoxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxine

Guidance literature:: Multi-step reaction with 11 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.

With pyridine; methanol; sodium hydroxide; oxalyl dichloride; Dowex 50W (H+); camphor-10-sulfonic acid; dihydrogen peroxide; sodium methylate; pyridinium p-toluenesulfonate; potassium hydride; sodium hydride; dimethyl sulfoxide; triethylamine; 3-chloro-benzenecarboperoxoic acid; 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

: 95791-13-2
(4aR,6R,7R,8S,8aR)-7-Benzyloxy-6-(3,3-dimethoxy-propyl)-8-methoxymethoxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxine

Guidance literature:: Multi-step reaction with 6 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.

With oxalyl dichloride; camphor-10-sulfonic acid; sodium methylate; pyridinium p-toluenesulfonate; potassium hydride; sodium hydride; dimethyl sulfoxide; triethylamine; In tetrahydrofuran; methanol; dichloromethane; chloroform;
DOI:10.1016/S0040-4020(01)86916-7

Reference yield:

: 95791-10-9
3-((1aS,2R,3aR,7aR,7bS)-6-Phenyl-hexahydro-1,3,5,7-tetraoxa-cyclopropa[a]naphthalen-2-yl)-propan-1-ol

: 95791-13-2
(4aR,6R,7R,8S,8aR)-7-Benzyloxy-6-(3,3-dimethoxy-propyl)-8-methoxymethoxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxine

Guidance literature:: Multi-step reaction with 4 steps

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

2: PPTS / CH₂Cl₂ / Ambient temperature

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

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

With oxalyl dichloride; pyridinium p-toluenesulfonate; potassium hydride; sodium hydride; dimethyl sulfoxide; triethylamine; In dichloromethane;
DOI:10.1016/S0040-4020(01)86916-7