3-((2R,4S,5R,6S)-4,5-Bis-benzyloxy-6-methoxy-3-methylene-tetrahydro-pyran-2-yl)-propionic acid tert-butyl ester

Base Information

Chemical Name:3-((2R,4S,5R,6S)-4,5-Bis-benzyloxy-6-methoxy-3-methylene-tetrahydro-pyran-2-yl)-propionic acid tert-butyl ester
CAS No.:176242-31-2
Molecular Formula:C₂₈H₃₆O₆
Molecular Weight:468.59
Hs Code.:

Synonyms:3-((2R,4S,5R,6S)-4,5-Bis-benzyloxy-6-methoxy-3-methylene-tetrahydro-pyran-2-yl)-propionic acid tert-butyl ester

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Chemical Property of 3-((2R,4S,5R,6S)-4,5-Bis-benzyloxy-6-methoxy-3-methylene-tetrahydro-pyran-2-yl)-propionic acid tert-butyl ester

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Technology Process of 3-((2R,4S,5R,6S)-4,5-Bis-benzyloxy-6-methoxy-3-methylene-tetrahydro-pyran-2-yl)-propionic acid tert-butyl ester

There total 6 articles about 3-((2R,4S,5R,6S)-4,5-Bis-benzyloxy-6-methoxy-3-methylene-tetrahydro-pyran-2-yl)-propionic acid tert-butyl 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: 70.0%

: 540-88-5
acetic acid tert-butyl ester

: 176242-30-1
Trifluoro-methanesulfonic acid (2S,4S,5R,6S)-4,5-bis-benzyloxy-6-methoxy-3-methylene-tetrahydro-pyran-2-ylmethyl ester

: 176242-31-2
3-((2R,4S,5R,6S)-4,5-Bis-benzyloxy-6-methoxy-3-methylene-tetrahydro-pyran-2-yl)-propionic acid tert-butyl ester

Guidance literature:: With lithium diisopropyl amide; In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide; at -78 ℃;
DOI:10.1016/0040-4039(96)00046-9

Reference yield:

: 127239-16-1
methyl 2,3-di-O-benzyl-6-O-(p-methoxybenzyl)-α-D-xylohexopyranosid-4-ulose

: 176242-31-2
3-((2R,4S,5R,6S)-4,5-Bis-benzyloxy-6-methoxy-3-methylene-tetrahydro-pyran-2-yl)-propionic acid tert-butyl ester

Guidance literature:: Multi-step reaction with 4 steps

1: n-BuLi / tetrahydrofuran / -40 deg C then 12 h, r.t.

2: CAN / acetonitrile; H₂O

3: pyridine / CH₂Cl₂ / -78 - 0 °C

4: 70 percent / LDA / tetrahydrofuran; hexamethylphosphoric acid triamide / -78 °C

With pyridine; n-butyllithium; ammonium cerium(IV) nitrate; lithium diisopropyl amide; In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide; dichloromethane; water; acetonitrile;
DOI:10.1016/0040-4039(96)00046-9

Reference yield:

: 90633-94-6,94827-30-2,90633-89-9
methyl 2,3-di-O-benzyl-6-O-(4-methoxybenzyl)-α-D-glucopyranoside

: 176242-31-2
3-((2R,4S,5R,6S)-4,5-Bis-benzyloxy-6-methoxy-3-methylene-tetrahydro-pyran-2-yl)-propionic acid tert-butyl ester

Guidance literature:: Multi-step reaction with 5 steps

1: (COCl)2, DMSO, Et₃N / CH₂Cl₂ / -60 °C

2: n-BuLi / tetrahydrofuran / -40 deg C then 12 h, r.t.

3: CAN / acetonitrile; H₂O

4: pyridine / CH₂Cl₂ / -78 - 0 °C

5: 70 percent / LDA / tetrahydrofuran; hexamethylphosphoric acid triamide / -78 °C

With pyridine; n-butyllithium; oxalyl dichloride; ammonium cerium(IV) nitrate; dimethyl sulfoxide; triethylamine; lithium diisopropyl amide; In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide; dichloromethane; water; acetonitrile;
DOI:10.1016/0040-4039(96)00046-9