[(3aR,4S,5aS,8R,9aS,9bS)-4-Hydroxymethyl-2-(4-methoxy-phenyl)-octahydro-[1,3]dioxolo[4,5-d]pyrano[3,2-b]pyran-8-yl]-acetic acid methyl ester

Base Information

• Chemical Name: [(3aR,4S,5aS,8R,9aS,9bS)-4-Hydroxymethyl-2-(4-methoxy-phenyl)-octahydro-[1,3]dioxolo[4,5-d]pyrano[3,2-b]pyran-8-yl]-acetic acid methyl ester
• CAS No.: 113466-59-4
• Molecular Formula: C₂₀H₂₆O₈
• Molecular Weight: 394.422
• Mol file: 113466-59-4.mol

Synonyms:

Chemical Property of [(3aR,4S,5aS,8R,9aS,9bS)-4-Hydroxymethyl-2-(4-methoxy-phenyl)-octahydro-[1,3]dioxolo[4,5-d]pyrano[3,2-b]pyran-8-yl]-acetic acid methyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of [(3aR,4S,5aS,8R,9aS,9bS)-4-Hydroxymethyl-2-(4-methoxy-phenyl)-octahydro-[1,3]dioxolo[4,5-d]pyrano[3,2-b]pyran-8-yl]-acetic acid methyl ester

There total 8 articles about [(3aR,4S,5aS,8R,9aS,9bS)-4-Hydroxymethyl-2-(4-methoxy-phenyl)-octahydro-[1,3]dioxolo[4,5-d]pyrano[3,2-b]pyran-8-yl]-acetic acid methyl ester 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,3R,4S,5S,6S)-2-Allyl-6-(tert-butyl-dimethyl-silanyloxymethyl)-tetrahydro-pyran-3,4,5-triol → [(3aR,4S,5aS,8R,9aS,9bS)-4-Hydroxymethyl-2-(4-methoxy-phenyl)-octahydro-[1,3]dioxolo[4,5-d]pyrano[3,2-b]pyran-8-yl]-acetic acid methyl ester (113466-59-4)

Guidance literature:

Multi-step reaction with 5 steps

1: DMAP / pyridine / 50 °C

2: 1.) BH₃*(Me)2S; 2.) H₂O₂ / 1.) EtOAc, THF, 0 deg C; 2.) aq. NaOH

4: CH₂Cl₂ / 0 °C

With dmap; dimethylsulfide borane complex; dihydrogen peroxide; In pyridine; dichloromethane;

DOI:10.1016/S0040-4039(00)96327-5

Reference yield:

Acetic acid (2S,3S,4S,5R,6S)-3,5-diacetoxy-2-allyl-6-(tert-butyl-dimethyl-silanyloxymethyl)-tetrahydro-pyran-4-yl ester → [(3aR,4S,5aS,8R,9aS,9bS)-4-Hydroxymethyl-2-(4-methoxy-phenyl)-octahydro-[1,3]dioxolo[4,5-d]pyrano[3,2-b]pyran-8-yl]-acetic acid methyl ester (113466-59-4)

Guidance literature:

Multi-step reaction with 4 steps

1: 1.) BH₃*(Me)2S; 2.) H₂O₂ / 1.) EtOAc, THF, 0 deg C; 2.) aq. NaOH

3: CH₂Cl₂ / 0 °C

With dimethylsulfide borane complex; dihydrogen peroxide; In dichloromethane;

DOI:10.1016/S0040-4039(00)96327-5

Reference yield:

((2S,3R,4S,5S,6S)-6-Allyl-3,4,5-tris-benzyloxy-tetrahydro-pyran-2-yl)-methanol (82614-11-7,133697-15-1) → [(3aR,4S,5aS,8R,9aS,9bS)-4-Hydroxymethyl-2-(4-methoxy-phenyl)-octahydro-[1,3]dioxolo[4,5-d]pyrano[3,2-b]pyran-8-yl]-acetic acid methyl ester (113466-59-4)

Guidance literature:

Multi-step reaction with 7 steps

1: DMAP / pyridine; CH₂Cl₂ / 40 °C

2: Li, liq. NH₃ / tetrahydrofuran / -78 °C

3: DMAP / pyridine / 50 °C

4: 1.) BH₃*(Me)2S; 2.) H₂O₂ / 1.) EtOAc, THF, 0 deg C; 2.) aq. NaOH

6: CH₂Cl₂ / 0 °C

With dmap; dimethylsulfide borane complex; ammonia; dihydrogen peroxide; lithium; In tetrahydrofuran; pyridine; dichloromethane;

DOI:10.1016/S0040-4039(00)96327-5

upstream raw materials:

p-Anisaldehyde dimethyl acetal

(E)-5-[(2S,3S,4S,5R,6S)-3,4,5-Triacetoxy-6-(tert-butyl-dimethyl-silanyloxymethyl)-tetrahydro-pyran-2-yl]-pent-2-enoic acid methyl ester

((2S,3R,4S,5S,6S)-6-Allyl-3,4,5-tris-benzyloxy-tetrahydro-pyran-2-yl)-methanol

Acetic acid (2S,3R,4S,5S,6S)-6-allyl-3,4,5-tris-benzyloxy-tetrahydro-pyran-2-ylmethyl ester

Downstream raw materials:

[(3aR,4S,5aS,8R,9aS,9bS)-4-[(S)-1-Hydroxy-3-(2-pentyl-[1,3]dioxan-2-yl)-prop-2-ynyl]-2-(4-methoxy-phenyl)-octahydro-[1,3]dioxolo[4,5-d]pyrano[3,2-b]pyran-8-yl]-acetic acid methyl ester

[(3aR,4S,5aS,8R,9aS,9bS)-4-[(R)-1-Hydroxy-3-(2-pentyl-[1,3]dioxan-2-yl)-prop-2-ynyl]-2-(4-methoxy-phenyl)-octahydro-[1,3]dioxolo[4,5-d]pyrano[3,2-b]pyran-8-yl]-acetic acid methyl ester