(3aR,4aR,6S,7R,8S,8aR,8bR)-6,8a-Bis-benzyloxy-7,8-bis-benzyloxymethyl-2,2,7-trimethyl-octahydro-benzo[4,5]furo[2,3-d][1,3]dioxole

Base Information

• Chemical Name: (3aR,4aR,6S,7R,8S,8aR,8bR)-6,8a-Bis-benzyloxy-7,8-bis-benzyloxymethyl-2,2,7-trimethyl-octahydro-benzo[4,5]furo[2,3-d][1,3]dioxole
• CAS No.: 479669-01-7
• Molecular Formula: C₄₂H₄₈O₇
• Molecular Weight: 664.839
• Mol file: 479669-01-7.mol

Synonyms:(3aR,4aR,6S,7R,8S,8aR,8bR)-6,8a-Bis-benzyloxy-7,8-bis-benzyloxymethyl-2,2,7-trimethyl-octahydro-benzo[4,5]furo[2,3-d][1,3]dioxole

Chemical Property of (3aR,4aR,6S,7R,8S,8aR,8bR)-6,8a-Bis-benzyloxy-7,8-bis-benzyloxymethyl-2,2,7-trimethyl-octahydro-benzo[4,5]furo[2,3-d][1,3]dioxole

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3aR,4aR,6S,7R,8S,8aR,8bR)-6,8a-Bis-benzyloxy-7,8-bis-benzyloxymethyl-2,2,7-trimethyl-octahydro-benzo[4,5]furo[2,3-d][1,3]dioxole

There total 12 articles about (3aR,4aR,6S,7R,8S,8aR,8bR)-6,8a-Bis-benzyloxy-7,8-bis-benzyloxymethyl-2,2,7-trimethyl-octahydro-benzo[4,5]furo[2,3-d][1,3]dioxole 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: 100.0%

benzyl bromide (100-39-0) + (3aR,4aR,6S,7R,8S,8aR,8bR)-7,8-Bis-hydroxymethyl-2,2,7-trimethyl-hexahydro-benzo[4,5]furo[2,3-d][1,3]dioxole-6,8a-diol (479669-00-6) → (3aR,4aR,6S,7R,8S,8aR,8bR)-6,8a-Bis-benzyloxy-7,8-bis-benzyloxymethyl-2,2,7-trimethyl-octahydro-benzo[4,5]furo[2,3-d][1,3]dioxole (479669-01-7)

Guidance literature:

With tetra-(n-butyl)ammonium iodide; In N,N-dimethyl-formamide; at 0 - 60 ℃;

DOI:10.1016/S0040-4039(02)02058-0

Reference yield:

1,2-O-Isopropylidene-6-O-triphenylmethyl-3-C-vinyl-α-D-allofuranose (322390-88-5) → (3aR,4aR,6S,7R,8S,8aR,8bR)-6,8a-Bis-benzyloxy-7,8-bis-benzyloxymethyl-2,2,7-trimethyl-octahydro-benzo[4,5]furo[2,3-d][1,3]dioxole (479669-01-7)

Guidance literature:

Multi-step reaction with 11 steps

1: 83 percent / DMAP / CH₂Cl₂ / 20 °C

2: 75 percent / Bu₃SnH; AIBN / toluene / Heating

3: 78 percent / Na / liquid ammonia; tetrahydrofuran / -78 °C

4: Dess-Martin periodinane / CH₂Cl₂ / 20 °C

5: tetrahydrofuran / 0 °C

6: 100 percent / Et₃N / CH₂Cl₂ / 20 °C

7: 58 percent / benzoyl peroxide / 3 h / Heating

8: 72 percent / dimethylsulfoxide / 120 °C

9: 65 percent / O₃; NaHCO₃; Me₂S / CH₂Cl₂ / -78 - 20 °C

10: 100 percent / LiAlH₄ / tetrahydrofuran / 0 - 50 °C

11: 100 percent / Bu₄NI / dimethylformamide / 0 - 60 °C

With dmap; lithium aluminium tetrahydride; dimethylsulfide; 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride; sodium; tetra-(n-butyl)ammonium iodide; sodium hydrogencarbonate; Dess-Martin periodane; ozone; triethylamine; dibenzoyl peroxide; In tetrahydrofuran; dichloromethane; ammonia; dimethyl sulfoxide; N,N-dimethyl-formamide; toluene;

DOI:10.1016/S0040-4039(02)02058-0

Reference yield:

((3aR,5R,6R,6aR)-6-Hydroxy-2,2-dimethyl-6-vinyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-acetaldehyde → (3aR,4aR,6S,7R,8S,8aR,8bR)-6,8a-Bis-benzyloxy-7,8-bis-benzyloxymethyl-2,2,7-trimethyl-octahydro-benzo[4,5]furo[2,3-d][1,3]dioxole (479669-01-7)

Guidance literature:

Multi-step reaction with 7 steps

1: tetrahydrofuran / 0 °C

2: 100 percent / Et₃N / CH₂Cl₂ / 20 °C

3: 58 percent / benzoyl peroxide / 3 h / Heating

4: 72 percent / dimethylsulfoxide / 120 °C

5: 65 percent / O₃; NaHCO₃; Me₂S / CH₂Cl₂ / -78 - 20 °C

6: 100 percent / LiAlH₄ / tetrahydrofuran / 0 - 50 °C

7: 100 percent / Bu₄NI / dimethylformamide / 0 - 60 °C

With lithium aluminium tetrahydride; dimethylsulfide; tetra-(n-butyl)ammonium iodide; sodium hydrogencarbonate; ozone; triethylamine; dibenzoyl peroxide; In tetrahydrofuran; dichloromethane; dimethyl sulfoxide; N,N-dimethyl-formamide;

DOI:10.1016/S0040-4039(02)02058-0

upstream raw materials:

benzyl bromide

(3aR,4aR,6S,7R,8S,8aR,8bR)-7,8-Bis-hydroxymethyl-2,2,7-trimethyl-hexahydro-benzo[4,5]furo[2,3-d][1,3]dioxole-6,8a-diol

1,2-O-Isopropylidene-6-O-triphenylmethyl-3-C-vinyl-α-D-allofuranose

(3aR,5R,6R,6aR)-5-(2-Hydroxy-ethyl)-2,2-dimethyl-6-vinyl-tetrahydro-furo[2,3-d][1,3]dioxol-6-ol

Downstream raw materials:

(1R,2S,3S,4R,5S)-2,5-Bis-benzyloxy-3,4-bis-benzyloxymethyl-2-hydroxymethyl-4-methyl-cyclohexanol