methyl 5-O--2,3-O-isopropylidene-5-C--β-D-allo- and α-L-talo-pentofuranoside

Base Information

• Chemical Name: methyl 5-O--2,3-O-isopropylidene-5-C--β-D-allo- and α-L-talo-pentofuranoside
• CAS No.: 102997-73-9
• Molecular Formula: C₂₀H₂₅N₂O₇PS
• Molecular Weight: 468.467

Synonyms:methyl 5-O--2,3-O-isopropylidene-5-C--β-D-allo- and α-L-talo-pentofuranoside

Chemical Property of methyl 5-O--2,3-O-isopropylidene-5-C--β-D-allo- and α-L-talo-pentofuranoside

Chemical Property:

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Technology Process of methyl 5-O--2,3-O-isopropylidene-5-C--β-D-allo- and α-L-talo-pentofuranoside

There total 3 articles about methyl 5-O--2,3-O-isopropylidene-5-C--β-D-allo- and α-L-talo-pentofuranoside 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: 93.0%

methyl 2,3-O-isopropylidene-5-C--β-D-allo- and α-L-talo-pentofuranoside (102997-71-7,102997-72-8) + 1,1'-Thiocarbonyldiimidazole (6160-65-2) → methyl 5-O--2,3-O-isopropylidene-5-C--β-D-allo- and α-L-talo-pentofuranoside (102997-73-9)

Guidance literature:

In 1,2-dichloro-ethane; at 90 ℃; for 0.5h;

DOI:10.1016/0008-6215(86)80051-9

Reference yield:

(3aR,4S,6R,6aR)-tetrahydro-6-methoxy-2,2-dimethylfuro-[3,4-d][1,3]dioxole-4-carbaldehyde (33985-40-9) → methyl 5-O--2,3-O-isopropylidene-5-C--β-D-allo- and α-L-talo-pentofuranoside (102997-73-9)

Guidance literature:

Multi-step reaction with 2 steps

1: Et₃N / 20 °C

2: toluene / Heating

With triethylamine; In toluene;

Reference yield:

methyl phenylphosphinate (7162-15-4,111469-75-1,121467-78-5) → methyl 5-O--2,3-O-isopropylidene-5-C--β-D-allo- and α-L-talo-pentofuranoside (102997-73-9)

Guidance literature:

Multi-step reaction with 2 steps

1: Et₃N / 20 °C

2: toluene / Heating

With triethylamine; In toluene;

upstream raw materials:

methyl 2,3-O-isopropylidene-5-C--β-D-allo- and α-L-talo-pentofuranoside

1,1'-Thiocarbonyldiimidazole

(3aR,4S,6R,6aR)-tetrahydro-6-methoxy-2,2-dimethylfuro-[3,4-d][1,3]dioxole-4-carbaldehyde

methyl phenylphosphinate

Downstream raw materials:

methyl 5-deoxy-2,3-O-isopropylidene-5-C--β-D-ribofuranoside

methyl 5-deoxy-2,3-O-isopropylidene-5-C-(phenylphosphinyl)-β-D-ribofuranoside

(3R,4R,5S)-1-Oxo-1-phenyl-1λ⁵-phosphinane-2,3,4,5-tetraol

1,2,3,4-tetra-O-acetyl-5-deoxy-5-C-<(R)-phenylhosphinyl>-α-D-ribopyranose

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