(2R,3R,4R,5S,6R)-4,5-Bis-benzyloxy-6-benzyloxymethyl-3-(9H-fluoren-9-ylmethoxycarbonylamino)-tetrahydro-pyran-2-carboxylic acid benzyl ester

Base Information

Chemical Name:(2R,3R,4R,5S,6R)-4,5-Bis-benzyloxy-6-benzyloxymethyl-3-(9H-fluoren-9-ylmethoxycarbonylamino)-tetrahydro-pyran-2-carboxylic acid benzyl ester
CAS No.:183742-61-2
Molecular Formula:C₅₀H₄₇NO₈
Molecular Weight:789.925
Hs Code.:

(2R,3R,4R,5S,6R)-4,5-Bis-benzyloxy-6-benzyloxymethyl-3-(9H-fluoren-9-ylmethoxycarbonylamino)-tetrahydro-pyran-2-carboxylic acid benzyl ester

Synonyms:(2R,3R,4R,5S,6R)-4,5-Bis-benzyloxy-6-benzyloxymethyl-3-(9H-fluoren-9-ylmethoxycarbonylamino)-tetrahydro-pyran-2-carboxylic acid benzyl ester

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Chemical Property of (2R,3R,4R,5S,6R)-4,5-Bis-benzyloxy-6-benzyloxymethyl-3-(9H-fluoren-9-ylmethoxycarbonylamino)-tetrahydro-pyran-2-carboxylic acid benzyl ester

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Technology Process of (2R,3R,4R,5S,6R)-4,5-Bis-benzyloxy-6-benzyloxymethyl-3-(9H-fluoren-9-ylmethoxycarbonylamino)-tetrahydro-pyran-2-carboxylic acid benzyl ester

There total 4 articles about (2R,3R,4R,5S,6R)-4,5-Bis-benzyloxy-6-benzyloxymethyl-3-(9H-fluoren-9-ylmethoxycarbonylamino)-tetrahydro-pyran-2-carboxylic acid benzyl 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:

: 2-amino-3,4,6-tri-O-benzyl-2-deoxy-D-glucopyranose hydrochloride

: 183742-61-2
(2R,3R,4R,5S,6R)-4,5-Bis-benzyloxy-6-benzyloxymethyl-3-(9H-fluoren-9-ylmethoxycarbonylamino)-tetrahydro-pyran-2-carboxylic acid benzyl ester

Guidance literature:: Multi-step reaction with 4 steps

1: 90 percent / aq. NaHCO₃ / methanol; CHCl₃; toluene / Ambient temperature

2: SOCl₂ / 0.5 h / Ambient temperature

3: 1.) Bu₃SnLi, 2.) BuLi

4: 1.) TMS-I, 2.) DIEA / 1.) MeCN, RT, 12 min, 2.) MeCN, THF, MeOH

With n-butyllithium; thionyl chloride; tri-n-butyltin lithium; trimethylsilyl iodide; sodium hydrogencarbonate; N-ethyl-N,N-diisopropylamine; In methanol; chloroform; toluene;
DOI:10.1021/ja961068a

Reference yield:

: ((2R,3R,4R,5S,6R)-4,5-Bis-benzyloxy-6-benzyloxymethyl-2-chloro-tetrahydro-pyran-3-yl)-carbamic acid benzyl ester

: 183742-61-2
(2R,3R,4R,5S,6R)-4,5-Bis-benzyloxy-6-benzyloxymethyl-3-(9H-fluoren-9-ylmethoxycarbonylamino)-tetrahydro-pyran-2-carboxylic acid benzyl ester

Guidance literature:: Multi-step reaction with 2 steps

1: 1.) Bu₃SnLi, 2.) BuLi

2: 1.) TMS-I, 2.) DIEA / 1.) MeCN, RT, 12 min, 2.) MeCN, THF, MeOH

With n-butyllithium; tri-n-butyltin lithium; trimethylsilyl iodide; N-ethyl-N,N-diisopropylamine;
DOI:10.1021/ja961068a

Reference yield:

: 3,4,6-tri-O-benzyl-2-benzyloxycarbonylamino-2-deoxy-D-glucopyranose

: 183742-61-2
(2R,3R,4R,5S,6R)-4,5-Bis-benzyloxy-6-benzyloxymethyl-3-(9H-fluoren-9-ylmethoxycarbonylamino)-tetrahydro-pyran-2-carboxylic acid benzyl ester

Guidance literature:: Multi-step reaction with 3 steps

1: SOCl₂ / 0.5 h / Ambient temperature

2: 1.) Bu₃SnLi, 2.) BuLi

3: 1.) TMS-I, 2.) DIEA / 1.) MeCN, RT, 12 min, 2.) MeCN, THF, MeOH

With n-butyllithium; thionyl chloride; tri-n-butyltin lithium; trimethylsilyl iodide; N-ethyl-N,N-diisopropylamine;
DOI:10.1021/ja961068a